Hmmm the good ol Mac vs. PC debate! WOO.
My first puter was an A500 bitd. Eventually it got replaced with Windows 3.1/Win95/Win98 etc. I've been using windows for about uh... 12 years. (I am Only 21!)
I'm used to it. I've been flailing around with it since 3.1! During that time I used a friends power mac also. It was OK, but we were like 10. It didn't matter. We just played Oregon Trail, Wolfenstein, and Gahan Wilson's Haunted House.
I bought a new Intel mac for the first time a few years ago. It was nice for awhile. Different GUI, looked and felt sleek...... but eventually I started to get annoyed. The marvel of a new shiney toy wore off. Some people get along fine in mac and make full use of all the software and whatnot. I didn't. I saw no real point for me to use an overpriced laptop to sit on the internet or use a text editor and GCC. A 486 thinkpad would have been functionally equivalent!
Mac is OK I guess, but it's no holy grail of OS's..a few of my problems:
- No equivalent to FruityLoops for same price range.
- No equivalent to NeoPaint (I dont like GIMP). I need PCX support that doesn't suck.
- My PC-Engine assembler has no mac version...
- games..... :(
I am comfortable with Windows since I have been using it for so long. Sure I have had the occasional hiccup from downloading something stupid... but it has always been extremely painless to fix. It wasn't the OS's fault either. It was my own from going to OMG1337warezd0wnl0adz.com and downloading and running an .exe without virus scanning it

.
I just recently did the Win7 jump. I love it. It runs smooth on both machines, the GUI doesn't have the same annoying things I found in XP (like the volume slider not appearing if you're actually doing a ton of crap), and it seems to play nice with some of the strange hardware I have.
Windows 7 runs all my old games. Diablo 2 runs on it. Doom 95, all the good stuff. And then there is DOSBOX for the even older stuff. The new games run great too (I built me a gaming PC). But for any SERIOUS gaming, I use the PS3 anymore. We're at the point where consoles are trumping PCs. But it is still nice to have a computer that has the option to. Mac's gaming options are limited at best. It may get better since they're Intel now.
The home macs are also not as user-openable and add-to-able. I like being able to crack the case open and start adding parts and doing all of that when I need to. Spare parts all over. Can't do that as simply with the Mac. But some people don't care about that. Some people never open their computer. *shrug*. I like doing all of that stuff though.
My other big complaint, and it's preference really, is OSX's gui. I grew to hate buttons on the left of windows, the lack of right click, the goony MIGHTY MOUSE, and that annoying Pinwheel of Doom when a program would tweak out. It's probably because I am used to windows.
In short, Windows is great for some, and Mac is great for some.
and then Windows blows for some, and Mac blows for some.
and if someone thinks they both blow, theres all the free Linux/stuff they can use.
All of the OS's provide the same basic functionality (file access/storage, productivity suites, browsing,chatting), so it boils down to picking which one gives you the nicest tickle in your pants when you use it.
my only real problem is the condescending OMG YOU USE PC? YOURE DUMB, MACS THE BEST. USE IT, WINDOWS IS CRAP, YOU DONT KNOW ANYTHING. nonsense. It makes the normal mac users look like idiots by association.