Want to know the ins and outs of how to sell your old iPhone? Were you one of the iPhone users who switched to Verizon now that it's finally available? Not sure what to do with your old AT&T iPhone? There are a number of things you can do with your old iPhone -- from using it as an iPod Touch to handing it down to family or friends -- but if you're looking to get some quick cash then there are a few things to know before getting started. Today we're going to show you how to throw out the old and bring in the new using a number of great services, just hit the jump to find out how!

When Apple and Verizon finally announced the iPhone would be available under the nation's largest network, Verizon subscribers across the country rejoiced. The same can be said for a hefty number of AT&T subscribers too, as a recent ChangeWave survey suggested a significant number of AT&T iPhone users would jump ship to Verizon once they had the iPhone.

So if you were one of the many AT&T subscribers who decided to go the Verizon route then here are a few quick tips to think about before putting your AT&T iPhone up for sale:

1. Jailbreak/Unlock: The iPhone usually sells for more money when it's jailbroken or unlocked, meaning you have the additional options of running restricted apps through Cydia or getting service on another carrier (like TMobile). If you are new to jailbreaking we suggest checking out the jailbreak forums, and we've also written up a few posts on how to jailbreak your iPhone on 4.1 firmware using Greenpois0n, Limera1n and PwnageTool.
2. Condition: It kind of goes without saying that you'll get more money if your device is in better condition, but this counts even more when it comes to the iPhone. If your device is in excellent shape, you're going to be able to ask for a higher amount. For example, an iPhone 3GS in 'fair' condition with wear and tear can get you around $230 while a 3GS in 'perfect' cosmetic condition can get you as much as $300. I've seen a wide range of pricing on the iPhone 4 and 3GS based on condition, so make sure you research prices and price competitively.
3. Wipe your data: Before you end up selling your old iPhone, we highly suggest you run a full data wipe on your device to make sure none of your data is available to the lucky new owner. We've done a quick How-To post to help you with the process.

Now that we're passed the basics and you're ready to put your iPhone up for sale, it's important to take a look at all the options you have before making a decision on which service to use.

There are a ton of great online services out there to help you sell your old iPhone and we won't be able to go through them all, so we've filtered down the list of services for you. We'll start with the most familiar of them all...

eBay

Selling your iPhone on eBay is a pretty simple process. If you've ever used eBay for selling things in the past then you know the selling process isn't all that tricky, however there are still some things to keep in mind when using eBay to sell your iPhone. For instance, eBay charges fees for each auction based on the item you're selling and how much it sells for, among other things, so here are five quick tips to help you get the most out of your auction:

1. Only ship to the buyer's confirmed Paypal address if using Paypal.
2. Price competitively if using Buy It Now as an option.
3. Make sure the pictures you use follow your description and are good quality -- post pictures of any physical blemishes on the iPhone and be up-front in your description.
4. Use a fast shipping service and make sure you include that in your item description.
5. Use keywords in your title and in your item description to attract more potential buyers.

You may also want to consider insuring your item in case anything goes wrong during shipping. Watch out for low-feedback buyers and also keep in mind that Paypal charges processing fees as well.

Craigslist

Selling on craigslist is locally based, so you'll be making a face-to-face exchange with someone in your area. I've used Craigslist to sell a number of things around the house, and always follow a few basic rules:

• Don't ever put your personal or home address in an ad. Ever!
• I'm usually fine with putting my personal phone number in an ad, but that's up to you. Some find it easier to text rather than email.
• Meet in a public place, preferably in the daytime.
• Watch out for email scams, something Craigslist is notorious for.

It's always a good idea to use caution when dealing with Craigslist. I've heard some pretty crazy stories of people getting robbed or worse when meeting with people for a transaction, so bring a friend and meet in an open, public area to avoid those types of situations.

Gazelle

Gazelle offers a service that lets you easily turn most electronic devices into cash. Simply send in your iPhone and Gazelle will send you money after confirming the item condition. The first thing you'll need to do is tell Gazelle what you're selling and what condition the item is in. You can choose from poor, fair, good or excellent condition, and it's important to be honest when rating the condition so there's no hiccups or snags along the way. It also helps if you have the box and original documentation and cables with your item, and the service will check for any water damages before giving you a quote.

An average-conditioned 16gb iPhone 4 will currently grab you about $280 where a perfect-conditioned iPhone 4 will get you as much as $360. The process takes about a week, and although you're not getting as much money in the end it's a great service if you don't want to deal with a lot of hassle. You can have your payment delivered through Paypal among other methods, and you can also submit multiple items if you're looking to get rid of a few more things while you're at it.

SellYourMac.com

SellYourMac.com offers a similar service to Gazelle by letting you send in your old iPhone for payment with little to no hassle involved. In a nutshell, they'll buy your old Mac or iOS device. You're required to provide pictures along with a serial number next to your item description and condition. Once SellYourMac.com receives your iPhone they clean it, inspect it and verify that it's in working condition before they turn around and sell it on eBay. Users can receive payment via Paypal and SellYourMac.com even says they give higher quotes than competing services like Gazelle, so you'll definitely want to compare before making any final decisions.

Verizon Trade-in

Verizon is also offering an iPhone trade-in program for current AT&T corporate customers who want to switch over. Verizon is offering the following quotes for older iPhone hardward:

• iPhone 2G – 16GB: $60
• iPhone 3G – 16GB: $105
• iPhone 3Gs 32GB: $160
• iPhone 4- 16GB: $280
• iPhone 4 – 32GB: $360

To the best of our knowledge Verizon hasn't clarified if they'll be making this service available to all AT&T subscribers or just to corporate customers, so make sure you give your Verizon rep a call to get more details on the incentive.

Bonus Tip: If you're going with Craigslist or eBay, another tip worth mentioning is to include all packaging, cables and adapters if possible. If you have any extra cases or accessories you want to throw in the deal it can usually net you a higher selling price as a bundle instead of trying to sell them individually.

Now that the iPhone is finally on Verizon, the time to start planning on how to dump your old iPhone is now. So whether it's eBay, Criagslist or any other method for selling your old AT&T iPhone we hope this article will help you along the way. As always, let us know if you have any questions or additional suggestions in the comments below!

Tips of the day will range from beginner-level 101 to advanced-level ninjary. If you already know this tip, keep the link handy as a quick way to help a friend. If you have a tip of your own you’d like to suggest, add them to the comments or send them in to news@tipb.com. (If it’s especially awesome and previously unknown to us, we’ll even give ya a reward…)

"Hello, Apple? HSBC here. World's largest company, maybe you've heard of us? Good, yeah, we'd like to place an order for the iPhone... How many? How about 200,000 for starters, b'okay?"

Sure, maybe the call won't go exactly like that, but ZDNet Australia (via MacRumors) is claiming the call may just be coming. Says HSBC's Australia and New Zealand chief information officer, Brenton Hush:

We are actually reviewing iPhones from a HSBC Group perspective ... and when I say that, I mean globally."

Will the Hong Kong Shanghai Banking Corp. really quit the Crackberry for a container truck (or ten) of Cupertino's finest? Only time will tell, but one thing's for certain: if RIM honcho Mike Lazaridis was feeling pressure from the iPhone 3G before, this type of rumor must certainly be turning it up a couple gravitational field levels...

[Note: This a a Wait-A-Thon post! Comment on this post -- or any post tagged "Wait-a-Thon" -- for your chance to win a $100 iTunes Gift Card! Note that you must post with a valid and real email address so we can send you your prize -- no switching!]

More and more people are switching to the iPhone. They’re switching from Palm and Windows Mobile and Blackberry smartphones to the iPhone. They’re switching carriers to get the iPhone. And now that the next-gen iPhone 3G is all but upon us, and more and more regions are announcing their plans and pricing, the switching is only going to get faster and more furious.

To celebrate the switchers, those who dare to phone different, the iPhone Blog wants to help you get your content off your old, perhaps restrictive and outdates systems, and onto your shiny, new iPhone.

We've already gone over how to move your music, movies, and other media to iTunes, so now it's time to get with the data: contacts, calendars, and email.

Read on to find out how!

This article assumes you’re switching from another smartphone, like Blackberry, Windows Mobile, or Palm, and are new to the iTunes + iPod (and iPhone!) ecosystem. It also assumes you're a dedicated Windows user or someone who just recently switched from Windows to the Mac and needs to transfer content to an iPhone.

Since longtime iPod (and Mac) aficionados will almost certainly already be using iTunes and the typical Mac applications, your iPhone will sync your content via iTunes the same as it would any other iPod. And, hey, if you’re a Linux (or any other *nix) user, I figure you’ve kept your content open from the get-go, and already know 18 different ways to get it onto your unlocked, jailbroken iPhone hax0red with Open Moko anyway...

"Push" First: Microsoft Exchange ActiveSync and Apple MobileMe

With iPhone firmware 2.0, everything changes. Why lead with this? Because if you intend to use either Exchange and/or MobileMe with your iPhone, you can read this section and you're pretty much done. (Or at least you can skip ahead to photos at the end -- though be sure to download iTunes anyway for your media). With Exchange and MobileMe (billed as Exchange for the rest of us), iTunes data sync is eliminated, cables are eliminated, and intermittent syncing becomes a thing of the past. With these "push" solutions, everything is automagically updated wirelessly (via WiFi or EDGE/HSPA cell network). Change something in Outlook and a few seconds later, your iPhone will show the same changes. Tweak some data on your iPhone, and a few seconds later, MobileMe's website will show the same tweak.

(Not using ActiveSync or MobileMe? No worries. Skip to the next section and we'll start setting up iTunes for local sync!)

So, to simply and easily set up most of your syncing using iPhone 2.0: tap Settings, tap Mail, Contacts, and Calendars (Just Mail if you're doing Exchange on iPhone 1.x), tap Add Account, and then select the type of account you would like to add.

Microsoft Exchange ActiveSync

ActiveSync makes its debut with iPhone 2.0, and doesn't function on the older, 1.x firmware, so if you intend to use it, make sure you have an iPhone 3G or have updated your original iPhone (2G) to the latest firmware as of July 11, 2008. To setup Exchange ActiveSync, tape the logo for it. If you're using Exchange 2007 on the back end, you may be able to automatically set up your account. If you can't, or are using an old version of Exchange -- or just in general due to the complex and fussy nature of setting up an Exchange account in general -- you're best practice is to check with your Exchange administrator (or hosted service provider).

Apple MobileMe (formerly .Mac)

MobileMe, Apple's replacement for .Mac and it's "Exchange for the Rest of Us". It will sync, wirelessly, over the air (OTA), contacts, calendars, mail, and photos between the iPhone and your Mac (with the aforementioned Address Book, iCal, Mail.app, and iPhoto) and/or PC (with Outlook). MobileMe will debut on July 11, 2008 alongside iPhone 3G and the 2.0 firmware, and should "just work" once you enter in your MobileMe username and password (previous users of .Mac will keep the same credentials, and will be able to use either user@mac.com or user@me.com interchangeably).

Local Sync: Getting iTunes

What Data Does iTunes Sync?

If you already have your data in Outlook, you're good to go for the iPhone. If you have it in another application, or scattered among a few applications... well, we'll get to that in a moment.

On the Mac side, iTunes "just works" with Apple's default applications, Address Book, iCal, Mail.app, Safari, and iPhoto, or with Microsoft's Entourage. Since sync services, contacts, calendaring, etc. are all "CoreServices" handled at the OS level, once you check the appropriate boxes in iTunes, the automagic process is almost transparent. You can even sync to Microsoft Office Entourage (Outlook's ugly step-sibling on the Mac side) by syncing Entourage with the default apps via CoreServices.

Similarly, if you don't have your data in these Mac apps yet, or have it scattered elsewhere, we'll also get to that in a moment.

Now let's break it down...

Syncing Your Contacts

These three protocols are all supported from directly within iTunes. If you have your contacts in one of them, simply choose the appropriate program from the drop-down in iTunes and your information will be moved right over to your iPhone.

From Apple OS X: Address Book, Yahoo! Address Book, and Google Contacts

On the Mac version of iTunes, you can check both Apple's Address Book and Yahoo! Address Book if you so choose. (I keep things simple -- and fear duplicates -- so I recommend picking one and sticking with it.)

If you're running OS X Leopard 10.5.3 or later, you can also sync your Gmail Contacts with your iPhone, using a more round-about method: launch Address Book, select Preferences from the Address Book menu, and check the box next to Synchronize with Google. Once set up, this will sync your Google Contacts to your Address Book, and then iTunes will sync them from Address Book to your iPhone.

From Everywhere Else: Thunderbird, Windows Live, Google Contacts

If you have your contacts in anything other than the above-mentioned programs or services, you'll have to move them over before you can sync them with the iPhone. Many programs/services allow you to export CSV files or vCards, including: Mozilla Thunderbird, Microsoft Windows Live, and Google Contacts.

Once you've got your export file, simply import the contacts back into Outlook, Address Book, Yahoo! Address Book and you're golden.

Syncing Your Calendar

For reasons known only to Apple and Microsoft, Outlook is your only calendar/event choice for syncing with the iPhone. (The drop down is so far only a merciless tease at options yet (maybe never?) to come).

From Apple OS X: iCal

Like Windows, OS X provides only one option for calendar sync: iCal (and not even a drop down to tease more.) Check it and go.

From Everywhere Else: Google Calendar, Windows Calendar, etc.

Many popular Calendar programs are compatible with the iCalendar format, which allows you to publish and/or subscribe from one program (and even platform) to another. Using this feature, you can try to move your data over your iPhone. Here's an example using Google Calendar:

You can subscribe to Google Calendars through Outlook on Windows, or use the Google Calendar Sync utility. Unfortunately the iPhone thus far doesn't reliably sync from anything besides the Outlook default Calendar, which means the subscribed Google Calendar doesn't get moved over unless you use a commercial product like the Paul Thurrott referenced SyncMyCal.

For Mac users a one way (Google to iPhone) work-around involves subscribing to your Google Calendar. From Google Calendar: Click on the Calendar Settings drop down, click on Private Address, and click on iCal to generate a private address for your Google Calendar especially designed for iCal. Copy the URL and open iCal. Inside iCal: Select the Calendar menu and click on Subscribe, then paste in the Private Address you copied from Google Calendar. Next time you sync, iCal will feed your Google Calendar to your iPhone. For bi-directional sync (Google to iPhone and iPhone to Google), there's the commercial Spanning Sync, and you can try the demo before you buy.

Theoretically, you could also try exporting and importing XML, CSV, or another cross-program file, although in my experience this often requires a vast amount of work (and Googling, and message board begging...)

Syncing Your Email

Two options for Windows users, the ubiquitous Outlook and Windows Mail (which I believe is an "upgrade" to the horrible Outlook Express rather a desktop version of the far superior WIndows Live Mail -- tsk tsk to both Apple and Microsoft).

From Apple OS X: Mail.app

Still only one choice from Apple OS X users, however: Apple's default mail client, the eponymous Mail.app. Again, just one checkbox, to keep with the ultra simple groove. (Usability over options is a mantra).

From Everywhere Else: Google Gmail, Yahoo! Mail, AOL, Microsoft Live/Hotmail, etc.

Yahoo! Mail can be setup as an IMAP email account on your iPhone, which means your Yahoo! Mail folders on your iPhone will exactly match your folders on Yahoo!'s website and vice versa. Also, Yahoo! provides "push" email for the iPhone, meaning changes to one will be reflected automatically and near-instantly in the other, just like Exchange ActiveSync and MobileMe (but without the calendar and contacts sync).

You can also set up your Gmail account, including the new Gmail IMAP service which works like Yahoo! Mail -- but without the "push" -- keeping your web, local client (i.e. Outlook, Mail, etc.), and web-based views synchronized at user-definable intervals (manually, every 10 minutes, etc.).

Unfortunately, since they don't (to the best of my knowledge) surface any open, standard protocols like IMAP or POP, Microsoft Live/Hotmail accounts can't easily be synced with the iPhone. Your options include signing up for a Yahoo! or Gmail account and manually moving the messages over to your new, IMAP-happy account, or you can try this free solution and see if it works for you.

For any ISP mail, you can simply set up the iPhone as a POP (or IMAP if they offer it -- much better!) client.

Syncing Your Bookmarks

iTunes supports syncing over all your bookmarks from Internet Explorer (hopefully the much more secure and standards friendly IE 7, right?) and Windows Safari (Apple's own browser). Hierarchies will be preserved, so think about how you'll use your booksmarks both on the desktop and the iPhone, and organize a good middle ground.

From Apple Mac OS X: Safari

No choices here. Check Safari and move along.

From Everywhere Else: Firefox, Opera, etc.

If you're using Firefox, Opera, or another Firefox-like (Mozilla Gecko powered), or Safari-like (Apple WebKit powered) browser, is to try and import your bookmarks into Internet Explorer or Safari (export first via HTML if you have to).

If you want to keep using Firefox (or another browser) for desktop use, there's no way to keep your bookmarks synced, unfortunately, but you can delete the IE or Safari bookmarks (since you're not using them) and re-import a fresh, updated set whenever you like.

Syncing Your Photos

For Windows users, the procedure to sync photos to the iPhone is as simple as it is non-powerful. Put all the photos you want to sync in a folder (or hierarchy of folders if you want to separate them out, e.g., Family, Friends, Birthday, etc.) and then select that folder in iTunes.

From Apple Mac OS X: iPhoto and Folder Sync

For Mac users, in addition to the folder sync described above, you can also chose to sync from Apple's iPhoto application, either your complete library, or from selected sub-libraries.

From Everywhere Else: Yahoo! Flickr, Facebook, Google Picasa, etc.

If you keep your photo collection online (i.e. Flickr, Facebook, Photoshop Express, Windows Live, etc.), you're going to have to target a desktop backup, or download the photos you want on your iPhone to a local directory. Put all the photos you want to sync in one folder, and make sure you note down the location of that folder (e.g. iPhone Photos). This will be the folder you target inside iTunes as described above.

For Picasa, make sure you organize all the pictures you want on your iPhone into one folder, or a hierachy of folders, and then that will be the folder your target from inside iTunes, also as described above.

Wait! Help! My Data is Stuck On My Phone!

From the Original iPhone (iPhone 2G) to iPhone 3G

Apple provides excellent directions for upgrading to the iPhone 3G.

From RIM Blackberry, Windows Mobile, and Palm Treo (Windows Mobile OS)

Blackberry's are data monsters. Data -- all of it, all now, all the time -- is the only reason for a Blackberry. It's why RIM invented the Blackberry. Windows Mobile, whether running on a Motorola, Samsung, HTC, Palm, or whatever device, is made to integrate with other Microsoft products like Exchange, ActiveSync, and Outlook/Entourage. (Note: Always make sure you have the latest/greatest firmware, patches, updates, etc. from your phone carrier and platform provider).

From a Blackberry or ActiveSync perspective, pretty much all business users will have an Exchange server of one kind or another available to them. Just use ActiveSync on your new iPhone 2.0 and you're good to go. (Check with IT if you have to, especially for the settings information).

If you don't have a business Exchange server but you do have access to a Windows computer with Microsoft Outlook on it, sync your Blackberry to Outlook, then Outlook to your iPhone.

For Mac users, check out Markspace, which provides a variety of phone-specific syncing solutions especially for the Mac. They're not free, but the time and effort they'll save you are well worth it. (I used to it get my data off a Palm OS Treo 680 into the default Apple apps and it worked seamlessly).

If you don' have any of the above available to you, try a hosted Exchange service, even temporarily. Sync your Blackberry data to that, then ActiveSync it to your new iPhone, and cancel the hosted Exchange service.

From Palm OS Treo

Palm OS (Garnet) Treo's can work similarly to the above if you have ActiveSync installed (or download it from Palm's website -- warning, direct file link!) and access to an Exchange server (business or hosted). 

Similarly if you have access to Outlook. If you're stuck in Palm Desktop, you'll first have to find your Palm install CD and go through the setup again, choosing Outlook instead.

(Mac users, see Markspace, above).

From a Feature Phone

If you don't have a smartphone, but are coming instead from a standard consumer feature phone (candybar or flip phone from Nokia, Motorola, Samsung, etc.) and have data on there you really don't want to retype, you can try looking for a data transfer kit that matches your phone. These vary widely in form, availability, and functionality, and will cost you money and time, but if you have both check out Howard Forums or even Google. Search and ask around. Be key word specific (i.e. "transfer data nokia model# outlook". Best of luck, and please share what you find in case others are trying out the same.

Conclusion

Well, there they are, my tips and tricks for getting your data off the old and outdated just in time for your brand new iPhone 3G/2.0. But try as I might, I know our readers — the real data ninjas — have a whole host of sneaky black magic all their own.

What are your best tips and tricks? Drop a comment and let us know!

[Note: This a a Wait-A-Thon post! Comment on this post -- or any post tagged "Wait-a-Thon" -- for your chance to win a $100 iTunes Gift Card! Note that you must post with a valid and real email address so we can send you your prize -- no switching!]

More and more people are switching to the iPhone. They’re switching from Palm and Windows Mobile and even Blackberry (looking at you, Barack Obama!) smartphones to the iPhone. They’re switching carriers to get the iPhone. They’re switching off the carrier-locks just to be able to switch to the iPhone in their own, currently unsupported countries. And now that the next-gen iPhone 3G is all but upon us, and more and more regions are announcing deals to offer it, the switching is only going to get faster and more furious.

To celebrate the switchers, those who dare to phone different, the iPhone Blog wants to help you get your content off your old, perhaps restrictive and outdates systems, and onto iTunes, ready to sync to your new iPhone.

Read on to find out how!

This article assumes you’re switching from another smartphone, like Blackberry, Windows Mobile, or Palm, and are new to the iTunes + iPod (and iPhone!) ecosystem. It also assumes you're a dedicated Windows user or someone who just recently switched from Windows to the Mac and needs to transfer content to iTunes.

Since longtime iPod (and Mac) aficionados will almost certainly already be using iTunes, your iPhone will sync your existing iTunes content the same as it would any other iPod. And, hey, if you’re a Linux (or any other *nix) user, I figure you’ve kept your content open from the get-go, and already know 18 different ways to get it onto your unlocked, jailbroken iPhone...

Getting iTunes

iTunes is a free download from apple.com and required before you can activate your retail iPhone. (And if your iPhone is unlocked, required before you can easily manage and sync content). If you don't already have it, go get it now. I'll wait. Honest.

Making the Most of Your Music

When you’re moving to the iPhone and iTunes ecosystem, the first and easiest content to move over is your digital music (stuff you’ve already bought, ripped from CD, or created yourself).

Moving MP3s and WMAs

First, we have to address the monster in the room -- DRM, which technically stands for Digital (Copy) Rights Management, though Draconian Restrictive Measures may be more accurate. It's a way of locking down content ostensibly to prevent piracy but often to frustrate legitimate users. For now, if you bought music from an online store like MSN Music, Yahoo Music, Zune Marketplace, etc. it's almost certainly got DRM that will prevent you from easily moving it to iTunes. Don't worry, I'll cover ways to work around it (for legitimate purposes only!) at the end of the article.

If your music is already DRM-free you're good to go and in an iTunes/iPhone supported format like MP3, just drag it over and drop it in (or choose File - Add to Library for you old school menu-lovers). For DRM-free/unprotected WMA (Windows Media Audio, the native format of Windows Media Player) music, while iTunes won’t play it, it will automatically convert it to an iTunes-friendly format for you. (See Ripping CDs, below, for details on how to chose iTunes conversion formats).

I recommend letting iTunes manage your library via Edit - Preferences - Advanced - General - Keep iTunes Music Organized and Copy files to iTunes Music folder when adding to library.

This puts your content into a logical file structure so you can more easily find individual files later with Windows Explorer, avoids wasting space with duplicate content, and prevents iTunes from losing track of something you added (for example off a USB drive) but forgot to copy locally.

Ripping CDs

If your music is on CD, iTunes will rip it straight to either MP3 or AAC (the successor to MP3 which has less support but arguably greater potential quality). Unless you’re tone deaf, I recommend ripping to at least 256 bit. You can set this via Edit - Preferences - Advanced - Importing - Import Using and Setting (Custom).

Buying Music Online

Want to buy music for you iPhone? iTunes is the #1 retailer now and provides nearly effortless browsing and purchasing options. Just hit the iTunes Store link in the sidebar and find what you like. For reason’s we'll get into in a moment, I heavily recommend buying only iTunes Plus music, which is the higher, 256 bit quality and DRM-free.

Though Apple CEO Steve Jobs has famously said iTunes would rather sell only DRM-free music, currently, EMI and independent labels are the only source of iTunes plus music. Sadly, to try and manipulate and fragment the market, Universal, Sony BMG, and Warner Music will only provide higher-quality, DRM-free music to iTunes competitors like Amazon MP3. But if you live in the US -- or when/if they expand the service internationally -- Amazon MP3 provides an iTunes friendly, if slightly more challenging to navigate, source for legit iPhone-compatible music.

Doing Your Best With Video

Unlike music, where MP3 is a pseudo-standard, CD ripping is mostly legal, and DRM is increasingly on the way out, video formats are far more fragmented, DVD ripping is mostly verboten, and DRM shows no signs of going anywhere anytime soon.

Moving MP4s, AVIs, WMVs, FLVs, Etc.

If you’ve shot your own videos, DVR'd, or otherwise created or acquired DRM-free video content, it’s only slightly more difficult to move them to iTunes than it is music. The “slightly” part being format. With a wide variety of containers, codecs, and the need to get both audio and video into exactly the right zen-like balance, using something like the free Videora iPhone converter for Windows or iSquint for Mac (or similar application) is almost a must. Open your existing video file, choose the iPhone setting, and let it convert.

Unless you have a fast machine, get a tasty beverage because it will take a while. And make sure you test a sample first, to prevent wasting a lot of time if your settings are off.

Already have, or already converted video content? Drag it into iTunes same as you did your music.

(Note: since iTunes doesn’t store video-type meta data in the video file itself, but rather in the iTunes database, if you want to have movies, TV shows, and music videos all filed in the right place, you’ll have to individually set them in each file’s properties under the Video tab.)

Ripping DVDs

Unlike music, where various “fair use” provisions exist that allow, in many jurisdictions, for you to rip your CDs to your computer, the DVD lobby has succeeded in making DVD ripping illegal in many parts -- the reason iTunes doesn’t provide that type of functionality itself.

If, however, you live in a place (or mindset?) that says when you legally buy a movie or TV show on DVD, you should be able to watch it regardless of whether its stays on a disk or moves to your hard drive, then open source software like Handbrake is your best friend. Handbrake will rip most DVDs straight to iPhone format, and add them to iTunes, in just a couple easy steps (navigate to your DVDs video directory, select the iPhone default, and let it rip!).

Bonus tip: make sure, especially when dealing with older movies, full screen movies, or TV shows, that you preview the video and choose de-interlace when necessary to prevent nasty scan-lines from showing up on your digitized video.

Buying Videos

Depending on what country you live in, iTunes provides movie rentals and downloadable movies, music videos, and TV shows. These are DRM-locked (see below) but perfectly compatible with the iPhone. Selection varies greatly from region to region, and some networks -- most famously NBC -- don’t see eye to eye with Apple’s less anti-consumer model, but until Apple unleashes its own DVR, this is the easiest way to get legit video on your iPhone.

Other Content

Big audio book fan? If you got them from Audible, simply go to Advanced - Authorize Audible Account, input your details, and drag-and-drop your audio books straight into iTunes.

Love podcasts, like our very own Phone Different podcast? Subscribe directly from the iTunes Store (or from the Subscribe via iTunes link from your favorite podcast's homepage). They’re free, come in audio and video (even HD!) and download straight into iTunes. While you’re there, be sure to check out iTunes University (also under the iTunes Store) for loads of free, and highly educational audio and video, from lectures to speeches to commencement addresses.

Dealing with DRM-Hell

Now for the hard part. If you previously bought music locked down with DRM, especially the more onerous DRM systems like PlaysForSure (or in MSN Music's case, PlaysNoMore!), there’s a little more work involved.

The Problem With DRM

What’s wrong with DRM? It does nothing to prevent real pirates (many of whom mass-produce content on boats in international waters or distribute online via massive criminal networks) and everything to frustrate regular, legitimate users who just want to upgrade their computers or move their content from one device or room to another.

We’ve all read the stories, from Google Video to Major League Baseball, to MSN Music. People, in good faith, spend their hard-earned money to buy the content they love, only to later get notification that the service they chose, from the vendors they trusted, will no longer “authorize” them to play back that content.

Imagine Tower Records going out of business and some men in black showing up to re-possess all the CDs and LPs (yes, we’re old enough to remember LPs, thank you!) that you ever bought from that store.

Sounds ridiculous, doesn’t it? But with digital content it's happened before and will happen again. Windows Media Player has also been known to automatically DRM music you rip from your own CDs if you’re not paying attention to the preference settings. So, if you’re stuck with previously bought or ripped DRM music, what can you do?

The Analog Hole

While from time to time DRM-stripping applications show up on the web, most DRM services are bound by their contracts with the big media companies to update the DRM as quickly as possible to render any circumvention obsolete. This makes DRM-stripping unreliable.

A more dependable, although technically “lossy” solution (i.e. some loss of quality will occur, though it will likely be negligible to all but audiophiles), is the infamous “analog hole”.

For music, simply use your old software (e.g. Window Media Player) to burn your DRM-locked WMA (or other format) music to playable CDs, and then use iTunes to rip those CDs back into digital format (preferably MP3).

Voila, the music you paid for, now ready for the device you chose to use it on.

Video is more of a challenge. If you’re an advanced user and have a Media Center PC (or two PCs, depending), with analog output and input, you can try routing your DRM-locked video out and back in, re-recording it like you would a VHS tape or analog cable TV signal. Provided you could then navigate the “black art” of video and audio containers and codecs, using something like the aforementioned Videora, for example, you could convert the captured video into iTunes/iPhone friendly MP4 H.264 format.

Advanced Capture

Even more advanced users willing to brave challenges like hardware acceleration and video layers? Capture software like CamStudio might let you avoid the digital-analog-digital loop. Your mileage, however -- and frustration level -- will vary.

An Ounce of Prevention

While Apple has among the most progressive DRM systems on the market, with the ability to sync any number of iPods to your iTunes, and authorize up to 5 computers to play your DRM-locked content (and the ability to call Apple for one-time re-downloads and re-authorizations should something go wrong), it’s vital to remember to BACK UP you iTunes content. USB hard drives are now ridiculously cheap and ridiculously big, so get one and copy everything to it, and update the copy regularly.

Also, burn playable CDs of all DRM-locked music and rip them back into iTunes so that, in case of system loss, re-install, or other catastrophic problems, you don’t have to worry about getting locked out of your own music.

Conclusion

Well, there they are, my tips and tricks for getting your content off the old and outdated and onto iTunes just in time for your brand new iPhone. But try as I might, I know our readers -- the real content ninjas -- have a whole host of sneaky black magic all their own.

What are your best tips and tricks? Drop a comment and let us know!