Oh my gosh, this is going to be your EIGHTH vote for an iPod Touch! If I were an advertising consultant for Apple, and they wanted me to come up with an ad campaign for the perfect customer for an iPod Touch, it would be YOU!
@pterhune, I don't think the inquirer is Apple-averse. He mentions wanting to sync up with his Apple Suite, and is interested in something that works with OSX.
What he's not keen on is getting an iPhone. He doesn't want to be tied to a big contract (doesn't trust the phone companies) and he doesn't necessarily need a smartphone.
Seriously, I can't think of a better product than the iPod Touch. It was designed JUST FOR this fellow!fellow!
My suggestion is to just stick with a relatively plain phone (maybe a pay-as-you-go option) and get an iTouch (iPod Touch). You can actually install Skype onto your iTouch so when you're home with wifi access, you can chat with people right from your iTouch.