Everyone has their preferences. Since 2K was supposed to be a "professional" OS, I imagine there might be a bit of attitude in some groups catering to those users (Kinda like asking about Poser in a Lightwave forum). I used 98 and NT before upgrading and didn't find anything confusing about 2K but then I've been fooling around with software since before DOS. I don't think there were any really significant changes to the kernel between 2K and XP. XP allowed Microsoft to marker a single core OS for consumer and professional use so the age isn't really a big factor in terms of the core OS. The primary factor, is will it run the applications you need. XP is probably going to be more appropriate if you have games or newer multimedia apps. K runs everything I need, including the ancient Falcon 4.0 flight simulator but other people's needs will differ. In my view, the system restore function is the best thing that XP has over 2K and certainly worthwhile. Either choice is vastly superior to 98. If you've got the bucks and don't mind the more limited software selection, get a Mac. If you're really adventurous, get Linux.

"Democracy is a pathetic belief in the collective wisdom of individual ignorance." - H. L. Mencken