Maybe someone with a PC can clue me in here as to how PC iTunes places the mp3 files. Ove on the Mac side you can keep your files in whatever folder structure you like and if you tell iTunes to automatically organize your music library it places them in Music Library > Artist > Album and complations get placed in Music Library > Compilations. Easy, simple, and logical folder structure and usually the way I'd organize mine. I manually manage my audio because I like to tag albums differently so my organization is left alone, but when I rip a new CD I know exactly where iTunes places the new files.
I find it hard to believe that anyone who is obsessive enough (I'm obsessive as well) about music to complain how iTunes organizes his music hasn't manually tagged his ripped music so its never an issue locating songs in iTunes. The tags are part of the files so moving computers doesn't destroy that info, and copying your playlist and pref files guarantees that playlist info isnt lost. Adding album art to music you ripped is easy as well and doesn't cost you anything.
Whether iTunes is better or worse is irrelevant, iTunes works differently from what you are used to and therein lies the issue. Perhaps you should have done more research before you bought the iP.
