There’s a wealth of free music out on the Internet that is actually perfectly legal to download: authorized bootlegs. This is live concert music recorded by fans – often plugged into the boards of the band, getting very high quality sound. The only downside is that fan sites that post these files often use the FLAC format, which makes for large downloads, and that can’t be played on most portable audio players.
The solution is the Magic Jelly Bean SHN Shortener. It takes FLAC files and converts them en masse to MP3 files of any specified bitrate. Very handy tool. It takes some time (maybe 30 seconds per song) and the UI for the MJBS is a little on the spartan side, but it’s a very straightforward program that does what I need it to do, and costs nothing. I’m currently working on converting some Elliot Smith and it’s working like a charm.