If iTunes is the only player you've been able to do this with, then you need to try more players, get a PC, or install Windows 2000.
I have a PC that is more powerful than my mac but I don't use it.
PC Players make it a pain to correctly fill in the metadata, therefore it is generally easier not to bother to have a clean, well-organized collection.
Windows version and what people told me.
iTunes on OS X is a much nicer experience than on PC, of course.
Besides, the fact Apple wants you to reencode your stuff sucks dick. Reencode my ass.
Why do you say they want you to re-encode? MP3 is perfectly supported, and all my collection is in MP3 format. Please look at this screenshot of the iTunes preferences I made 2 minutes ago:
http://img291.imageshack.us/img291/3199/itunespref3vq.jpg