I've found the coolest thing ever. Indy.TV is a music player similar to MusicMatch jukebox, except it's all independant music.
Essentially, it's a tool for discovering new independant music. You rate each song, and it learns what you like, then gives you more of it. It's free, and it's legal. You can keep copies of any of the mp3s you like, and do what you like with them. I'll be using this program quite a lot.