"Seriously, wtf. It's the most unorganized program ever, I freaking hate it"
sounds like the typical newbie to iTunes. Click on the image that looks like an eyeball in the lower right hand side of the iTunes application. Your music will then be classified by "Genre", "Artist", and "Album". I've found 95% of the people who don't like iTunes haven't found this basic feature. Personally I like iTunes better than any other application I've used such as Winamp, anapod explorer, musicmatch box, etc. And to reiterate what scott said, I think its pointless to use lossless files for any portable music player 99% of the time. I use shure e4's (retail for $300 got them for a little over $200) and given the listening environment, 256 aac files work fine for me and it allows me to keep a lot more music/shows on my iPod. U