Not to be a fly in the ointment, but I just gotta comment on this:
His life savings is wrapped up in his system and all those files. And it would be a serious problem if the audio quality was lessened... but he doesn't have the capacity to back up all the files at this point.
The technical term for this condition is MASSIVE STUPIDITY.
Your friend has "speakers that won't fit into your car" but he can't be bothered to go to an office supply store and drop $60-$100 on a external USB drive? That would hold 80-120GB of data?
Removable media has never been as cheap, copious, and easy to use as it is right now. There's really no excuse for having one and only one copy of ANY critical file sitting around without a backup. Much less an entire collection of them.
Do your firend the biggest favor you could ever do. Sit him down, and ask him how important the sound quality of his audio files is to him. Then ask him to imagine that the sound quality of every one of those precious files has suddenly dropped to ZERO. Ask him to imagine how he would feel if, after hearing a weird little click from inside his computer, he found that in that fraction of a second his entire music collection was simply GONE, corrupted, hopelessly unrecoverable. It can happen. No, actually IT WILL HAPPEN. Statistically it's just a question of when.
Then offer to go with him to the computer store or the office supplies store and pick out a nice, cheap, large USB hard drive, take it home and help him set it up. Don't leave him by himself until you're sure the backup software has run successfully.
Friends don't let friends compute without backups.