Uh oh, this truck **** just got real. Apparently my dad is really motivated to get something done. His current proposal is: He gives my $34,500 for my truck (I paid $39,000 for it brand new, 5 years ago), I use $9000 of that to pay off the remaining balance on my current truck loan. We both go to the dealer, and we buy 2 trucks, one for each of us. He has worked it out with the dealer that we can get 2 half ton, V-8, 4x4 loaded (heated leather, and absolutely gorgeous interior) for $39,000 each (they're listed at $48,000). And he will trade in 2 of his older pickups, one worth about $17,000, the other only $3000, towards his new truck.
It is convoluted, but in the end, I would be able to upgrade to a new truck, reduce my payments by about $300/month (and extend payments by about 3 years), and I'd work it so I would end up with $5000 left over, to pay off a high interest loan I have. I think it has turned into a no brainer, I don't like the payments for 3 more years, but they're reduced, and really, if I can get $34,500 for my current truck, it would be stupid to not take advantage of that.