[Jeff Higgins]

Sounds like your new found friend is just a bit irresponsible. He is "upside down" on his sled, owing more than it's worth. He totalled one, and that puts him in a position to where he can't afford to total another. He is trying to pawn some of his past irresponsibility off on you.

I would buy the e-bay sled and make him give you the totalled one. He gets to finish paying off the loan. That puts him in no worse position than when you found him. He gets the same or nicer sled in the end. This should not turn into an opportunity for him to profit because you feel bad. The parts value of the totalled sled is yours; you "bought" it from him when you totalled it. Tell him either that or all you pay is the deductible. Again, he should not profit from this, and you are not responsible for his past screw-ups that have led him to ask you to cover for him. And next time, don't get on it.