Tom,
That's a heckuva can of worms to open, ya know.
That said - If you really like fiddling with computers, you may or may not like it (true geeks will find the terminal pretty quick, but some Windows-y types don't like 'em). On the other hand, if you view your computer as something to get other things done (web surfing, e-mail, word processing, or whatever) and you want to do that with a minimum of computerese getting in the way, then a Mac is the best choice.
I'll make the same offer to you that I have to several other "switchers" on the board: If you have any issues, feel free to call me (PM for my number) and I'd be happy to help you out. FWIW, I can only think of one person who's ever called me, so that tells you that things generally work out very well and that the machines are very easy to use.
Now if only I could get my mom to get an iMac. She's got an "eMac" which is getting very long in the tooth, and I was showing her the ropes on her new iPhone today (which she actually went and bought without any prompting from me, amazingly enough) and I was like "man, this thing is SLOOOOOOOOW" and then I realized it doesn't even have USB 2.0 - Suddenly, the long syncs started to make sense!
