I've always liked Apple products, all the way back to preferring the Apple IIes to the IBMs back in the low tech computer lab in middle school, but I never bought one. My roommate my sophomore year of college had a Mac, and I liked that. However, John never wanted to get one because they don't make the computer games he likes for Macs, so we never bought one as a desktop. When I was looking for a laptop a couple of years ago, I really wanted to get a Mac, but couldn't quite justify the extra expense, because they were a lot more than my little Toshiba.
Then the iPod came along, and just about everyone I knew bought one. I got why people liked them, but the decent sized ones seemed too expensive. When my mom bought my brother an iPod as a graduation gift, I hated it. I was supposed to load songs on to it for him from John's extensive music collection. For whatever reason, I had a really hard time getting it to do that. I kept deleting things by mistake. And I hated the click wheel. So, no iPod for me.
When the iPhone came out, of course I thought it looked cool. But I have still have and like my little sidekick. Plus, again, it was too expensive, and I wasn't interested in switching to AT&T anyway.
Well, that all changed when one of my colleagues brought in his new iPod Touch to work to show off to the rest of us. Holy crap that thing is cool, and wow do I want one! The video looks amazing. The interface is so much better. And the size of the touch is just right. They are still kind of expensive, but I think I might have to get one. Steve Jobs, you've caught me at last.

My only problem with the iPod Touch is the storage size and the price. I'll stick with my old third generation iPod until the prices come down and the storage sizes go up.
Although I do dig the ability to surf the web on those suckers.
The scary thing is you used the Apple IIe in middle school. I used them in elementary, middle and my freshman year of high school - which, I may emphasize, was 10 years ago. aaack.
You should look into a mac desktop, cause now macs run on intel, and you can dual-boot into windows if you want.