You might be able to have your roommate authorize your pc on his itunes acc. When you do this, you can import ALL THE MUSIC/VIDS/WHATEVS. It will likely take a long time to d/l everything or you can pick and choose. I know if someone was going to sync my itunes, I would pick and choose stuff for them since I have been collecting these files since I was like 9... there is a lot of garbage in there.
Repeat with second roomie.
To authorize, have them sign into their itunes acc on your pc, have them authorize your pc, and then impport what you want, and sync you phone.