I've been using iTunes for quite a while now. I used to use winamp but when I got my iPod about 3 years ago there was no good alternatives to iTunes. iTunes has been giving me problems lately though. Biggest one is that it updates its library file whenever its done playing a song. This causes my computer to stall for 2~3 seconds. This has almost gotten me killed many times in FFXI.
I spent most of last night trying to find a way to fix it and short of deleting my library there isn't anything I can do. So I've been considering moving to another media player. Windows Media Player is out... just on principal. While its sad for me to say, Foobar is too complicated for me. I've been playing around with winamp this morning and not much has changed since I last used it, though there are some things that weren't around before that are very welcome.
However, I have another dilemma. I have put a lot of work into my iTunes library. Not only going through and cleaning up my tags, which are perfect, but also getting album art for all of them. I also have a rating system that I use and have a few playlists that I really like that are based off of that system. While I could setup something similar in winamp there I haven't been able to find a way to bring over this information from iTunes, so I would have to start over. Hopefully I'll have something figured out in the next few days.