When you buy an app or game in the App Store, book in the iBookstore, or music, movies or TV shows in iTunes, you're asked for your iTunes password before the transaction goes through and the download begins. That's important when there's money involved. As the great Smurf berry scandal of 2011 taught us, you can never be too careful when it comes to preventing unintentional or unauthorized purchases -- that's why Apple now requires a password for every in-app purchase. But what about when there's no money on the line? What about when you're not buying something but just downloading a free app or game, or free song or feature? Should iTunes still ask for your password? What about when you're simply updating an app or game? Should iTunes ask then?
Some people, really security conscious people, would probably prefer iTunes ask for a password any time it does anything, always. Better safe than sorry. Who knows who could be using your iPhone, iPod touch or iPad after all, from a friend to a colleague to a spouse to a child to a friend's colleague's spouse's child. You really want to risk $100 in Hello Kitty apps suddenly showing upon your Home screen?
Other people, really convenience-oriented people, would probably like iTunes to ask for a password as little as possible. Maybe never. If you're the only one who ever uses your iPhone, iPod touch or iPad, and it never leaves a place you control, then why should you be bothered by having to enter in a password every time an app has a minor bug fix update?
Personally, I'd like a choice (big surprise, right?) Give me a Settings option for "always ask", or "only ask for paid transactions". I don't think "never ask" is safe, so I'm fine with that not being there. What about you? How often do you think iTunes should ask for your password?