File sharing is a cinch. It's easy both ways - the only problems occur when you have to use a Windows machine to pull stuff off the Mac, but that's not due to the Mac. I actually do lots of filesharing over the wireless network at home because the printer attached to the PC is a couple years old, non-USB and has no Mac drivers, so I pull my Word files off the Mac via file sharing. You just have to turn it on, and it works seemlessly.
The coolest thing is that I only ever see drives I'm attached to. On Win2000 on my PC, this is not the case. It always shows the Mac whether it is attached or not. So, if I'm not sure, I'll click on it and get an error after a second.
A Windows directory mounts right on the desktop, and you disconnect by dragging the drive into the trash (which turns into an eject button the moment you drag something that is not deletable, like a CD-ROM).
As for games, there aren't as many on the Mac, and it depends what you like. They come later, although Warcraft 3 came at the same time as the PC. It also depends on what you like to play. There aren't as many shooters, but there are many strategy games. Civ3, Stronghold, etc. I also play Spiderman (not the movie one, the one before that). It seems that the gaming market on Mac will be increasing though, especially with OS X's success. I can't wait to see native Cocoa games (the native OS X API), and have been thinking about starting a company that develops games only for Mac and only in Cocoa.
Everything is easier on the Mac. You get used to shortcut keys and miss them when you use a PC. Most of the shortcuts are universal (such as Apple-Q) and wonderful.
While the system is certainly not crash proof, I've never managed to crash it, and I've tried to - mainly by clogging up the pipeline. The thing slowed to a crawl, but recovered when I forced the Terminal to quit.
I also am only running with 256MB on X, and have not experienced any slowdown. I also don't hear my HD constantly grinding - something that happens all the time on the Windows PC with 2000 Pro on it.
I will warn you, however, that if you use one of these things a lot, you will be very unhappy when you use a PC, especially when something goes wrong. A few days ago, I needed to scan things and my older scanner, once again, didn't have Mac drivers. I spent an hour getting it to work - and ended up getting Win2000 really ticked at me. If I had a scanner that was Mac friendly, it would have been literally plug'n'play.
It may take time to get a bunch of hardware for your Mac, especially if you've been a PC user for years, but it's worth it. OS X isn't perfect, but it holds a lot more promise than Windows and Apple's control over hardware and software helps maintain greater stability and quality. I've gone from a true blue Mac basher (hated them before X - but was really ignorant) to a Mac user and proponent. Nearly five months down the line, I'm still excited about my Mac. I can't remember being this excited about a machine for this long. I hadn't been excited about a computer for years, but this little iBook is so wonderful because it does what a computer should do - it works. It's literally saved me 2-3 hours a week in time spent trying to fix problems. Now, if I can get my friends to switch, it'll save more time - because I'm always fixing their computers for them. Many of them have seen my contentedness and decided that their next machine will be a Mac. Most everyone who sees me with the little notebook, after talking with me, also say that the now want a Mac. I really think that Apple's marketshare will increase when the market rebounds, and that means more games and more software.