The biggest issue with this was that though we no longer pirate music from anyone, we had a sizable collection of friend's files and even stuff I downloaded seven years ago in the Napster heyday. We came to the conclusion that even retaining these files was pretty immoral.
I deleted everything (save some non-stolen files and protected iTunes store AACs) and started from scratch.
Yesterday, I took a bunch of old CDs that we no longer wanted to Newbury Comics to cash them in. They took a few of them and gave me $39. I put every last bit of it toward repurchasing some of the music that we had been missing:
Jack Johnson - Brushfire Fairytales
Barenaked Ladies - Maroon
Ben Folds Five - The Unauthorized Biography of Reinhold Messner
Beck - Midnight Vultures
I still very much miss:
The Shins - Oh, Inverted World
Wilco - Yankee Hotel Foxtrot
The Flaming Lips - Yoshimi Battles the Pink Robots
Death Cab for Cutie - Something about Airplanes
and all five Dismemberment Plan discs
It feels really good to listen to this stuff knowing that the artist was finally compensated (not that I don't have serious issues with the state of the industry and the extremely questionable practices of the RIAA).