So I think I know my own answer but want to gauge any feedback or unknown risks with this thread. I have a vehicle leased through Chase which I can’t transfer. I’ve got 6 payments left and just found my dream car (used) so I went ahead and bought it.
The best trade in offer I got was about $2500 underwater, and the remaining payments on the car + the registration which will need to be renwed in October (~$100) + disposition will be around $3200 if I keep it. If I sell it to Carvana I’ll also get about $500 back in insurance premiums, so my breakeven loss is about $2k at this very moment. It seems that used car prices are currently being propped up by Covid, not sure how long that momentum will last for if I decide to keep the car for another few weeks.
My sister as well as a close friend of my wifes (Maid of Honor) both relocated from NYC to Long Island and could use a car, so both have expressed interest in possibly “taking it over” - with the full understanding that this is a long term borrow and I’m now the one fully at risk if they crash it, damage it, etc.
My sister likely can’t afford the full payment, but I have a stronger conviction if anything went wrong over the next few months they’d own up and cover any additional damages or issues, and she carries her own insurance.
My wife’s friend would probably pay the full payment, but I don’t believe she has her own insurance because she usually drives her moms car. To me, that is the bigger red flag so any big damage seems too risky (although she has very afflulent parents, but I’m not sure that they would necessarily bail her out).
My gut tells me that unless my sister wants it, I’m better off just eating the loss. But if I could avoid losing $2K that’s obviously my preferred options.