For the last few months I've been conducting an experiment, trying to figure out whether it better suited my needs to sync my iPhone 3G to my desktop computer, to my laptop, or to embrace the (potential) future and try to sync only over-the-air with the cloud (online services and storage).

First, a little about the contenders.

  • My MacBook is purposefully kept light. Aside from whatever temporary I'm working on at the time, it has almost nothing on it, including no media unless I'm actively watching it. It's speed on-the-go with limited capacity.
  • My iMac is heavy duty and also serves as my media machine. It's connected on one end to a Drobo and serves an Apple TV in the living room on the other. It's pure power and content, but absolutely no portability.
  • My cloud is, well, the cloud -- everything I keep on my MobileMe, iDisk and Apple keeps ready for me on their massive iTunes servers.

A month with each of them (Round Robin interuptus notwithstanding) and what were my results? Which have I stuck with (for now)? Read on to find out!

Syncing the iPhone with a Laptop

The laptop is a convenient sync-solution to be sure. It goes almost everywhere I go, so it's almost always available. If I get new content, be it a new podcast or a new iTunes movie, I can immediately plug my iPhone in and sync it over. This is one heckuva compelling argument, even more so prior to iPhone OS 2.2, when the iPhone itself couldn't directly download new podcasts. It also makes for easy charging on-the-go. There's always a USB port available, and I don't have to worry about iTunes wiping out my current content to "helpful" prepare for syncing with a different machine. Have a problem? If Apple pushes out a firmware update, or -- horror of horrors -- I need to restore, the laptop being mother-ship, means I can handle it right away -- no waiting to get home to re-load everything.

The downside? My laptop hard drive is small. My old laptop had a tiny 100GB 7200RPM drive (I went for speed over size) and my new one has a 128GB. With the OS, applications, data, etc. (sometimes virtual machines), that leaves precious little space for media files. This meant I was always in "management" mode. I could keep a small subsection of my laptop, either subscribing to a few of the same podcasts I already subscribed to on my iMac, or moving files back and forth when I was on my home network (or, in a pinch, slooooowly over iDisk). This reduced the convenience and eliminated one of the best features of the Apple ecosystem -- the ability for it to keep track of what you've watched and how much of it you've watched across platforms. Duplicate files throw that out the window.

Syncing the iPhone with a Desktop

The desktop is a powerhouse. Big drives, lots of ports, and in my case it already serves up content to my Apple TV. That means what I want to watch and listen to it is already loaded up -- and because it's on most of the time, is constantly downloading new podcasts and other content. I can wake up in the morning, plug in, and get the latest stuff, maybe move over a TV show or movie if I want to go somewhere later and watch something (via the iPhone AV-out cables -- like a portable Apple TV!). And then when I get home at night, I can sync up again and continue watching/listening to anything I haven't finished yet via Apple TV or AirTunes speakers (and thanks to the iPhone Remote App, I can control it from anywhere in my home), from right where I left off.

Limitations? You betcha! Aside from not having my host machine with me while I'm away from home -- meaning I can't get new stuff when I want it -- if I ever decide to rent HD content (or create my own with an HD camcorder) or subscribe to HD podcast feeds to really make use of the Apple TV's 720p output, those won't transfer over to the iPhone. If I subscribe to both HD and iPod feed, then I have the same content duplication problem. Granted, for most podcasts the iPod version is fine, but when we get into TV Shows and especially movies, it just won't cut it anymore.

Syncing the iPhone with the Cloud

Since iPhone OS 2.0, with MobileMe and Exchange ActiveSync support, both my work and personal email, calendar, and contacts have been syncing with the cloud, and I've been able to buy wirelessly from the App Store (2G/3G for under 10MB, WiFi for over). That was step 1 in my considering living foot-loose and tether-free. iPhone OS 2.2 was step 2: over-the-air (OTA) podcast downloads (with the same 10MB cell/WiFi split). Sure, I'm skipping the iTunes music store, but I don't buy music anywhere near are often as I get Apps or download podcasts. If I'm out and about, without desktop or even laptop, and I find out a great new podcast has just dropped, I can either hit the "get more episodes" link, or just search for it in the iTunes App and download it directly to my iPhone. With apps like MobileFiles, I can even access my iDisk to view my docs and even transfer them to my local iPhone storage.

Need more? Yeah, I'm still waiting on Apple revamp MobileMe and add push support for Task, Note, Photo, and Backup, syncing as it looks like Microsoft is about ready to do with Windows Mobile 6.5's "My Phone" feature (cute name!) Bandwidth limitations, however, make me think I won't be getting OTA TV show or movie downloads anytime soon. Given the size of firmware updates, they too will likely remain tether-only for now. Also, just like I can be caught away from a laptop or PC, even WiFi and cell coverage have their limits.

Conclusion

After having tried these three different sync solutions, each on their own, which one have I decided on? Which one is the clear winner?

None. Frankly, each one has advantages and disadvantages, so I've evolved into a hybrid model. My iPhone is setup on my iMac desktop and I sync there fairly regularly. Due to the advances in iPhone OS 2.0 and 2.2, however, I don't sync anywhere nearly as often as I used to, and if I need new content while I'm away, I just download it directly (for podcasts) or drop it into my iDisk (for other types of small media -- using Back to My Mac from my laptop).

It's not completely elegant and seamless yet, granted, but it's amazing how far we've come even just recently, and while "sync is hard", I have every confidence future iPhone and MobileMe updates will make it easier and easier over time.

So What Do You Do?

Sync from your desktop? From your laptop? Pure cloud baby? Or, like me, do you keep a couple tools at the ready? Let me know what you're doing, especially if you have any ninja-sync skills you wouldn't mind sharing!