Like a few have mentioned before, I don't like the whole taking ownership of people's PC problems. It seems once you touch a computer once, it's your problem from that date on.
Regarding the OP's issue...I just backup complete profiles anytime I need to do a re-image, that is anything other than large collections of videos or music that isn't needed or would take too much time to restore. I hold onto the data for about a week and then follow-up to find out if I can delete it.
If the user is especially difficult to deal with I'll even take a screenshot of their desktop before-hand, because they love to tell you things were "right on their desktop" before you imaged it.
I gave up trying to convince people to organize long ago, and I've seen employees get fired for losing data, so I'm not playing that game.