Mac user and general gadget whore here with many hours spent fiddling with various operating systems.

If you're a hardcore Apple nut, nothing is going to compare with the integration of Apple's platforms. Buy an Apple device, and a few minutes later it's all synced up with your Apple life. That's nice, but it comes at the price of Apple deciding what is best for you. Yes, I've heard about google's ability to sync, but blending all your apps and data between a desktop, laptop and phone is just way easier on Apple.

I have desktop units running OSX, but they are built from common PC parts, they also run Windows and Linux at the same time. I have a MacBook Pro laptop because it's simply the nicest notebook computer on the market for the best price. I have a Windows Mobile phone because (at this time) it has the best GPS and mobile apps available. I have a 7" Android tablet because the iPad is far too much money for something I mostly only use in the shitter.

Is Android going to work well with your mac life? Hell no, that's why they want you on Gmail and Gdocs and all the other Google services. Your iPhoto albums, iCals, iDisk etc. are Apple services and that's the way Apple keeps you on their hardware. I'm sure you can make a successful switch to Android, but it's not going to be without a bit of a struggle.

Three years of happiness with a 2g iPhone and you're going to abandon the platform just because of a little hiccup with the rules in the US? Why not buy a legal iPhone in Hong Kong that can be used worldwide with any carrier or sim card instead of jailbreaking and hacking one. You could also choose a different carrier in the US for the short period of time you stay there.

I think a WinMo user switching to Android is going to be very, very happy. I think a heavy Mac user with an iPhone is going to find the move less satisfying because of the Apple to Google conversion process. Remember, nice Android devices are expensive too, so you're paying good money to force your move to google.

Cheers!
ChinaV