I had major problems with iTunes when I was using it on a PC, and I found that with each new version of iTunes, it became more difficult to use with a PC.
I bought a mac book for the sole purpose of managing my music collection on iTunes, and all my problems went away. I uploaded all the CD's that I currently had and I now purchase most of my music on iTunes. I have not had any of the problems mentioned in the previous posts. You can import whatever artwork you want, you can re-name albums or songs to arrange them anyway you want, and in terms of albums where the songs are indexed but should all run together you can choose zero gap in between songs when you import them. Plus, you can import your CD's and downloads using the loss-less option, so the sound quality is great. I hated ITunes for a while, but now I'm a huge proponent. I also have Apple TV, which streams your music collection through your TV making it into a virtual jukebox for a party. One trick on organizing your collection is to select the album icon view (not cover-flow) from there, you can choose to arrange by three parameters. I go by artist, album, year, and it works perfect; then I switch back to cover flow and it maintains the order.
The only thing I miss is the tangible aspect of a CD or album, so I've started collecting used records again from a local record store that sells a ton of used records all for a dollar.
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