Hi everyone. Thank you again for all the great feedback. For those interested, here's some more details:
- He is in his mid fifties.
- He is being treated for depression, both clinically and with medicine.
- No real option to move in with family. Family is very small and all locations are saturated.
- He came to me expressing interest in getting better with financial responsibility, feeling he hit rock bottom. (But since it's happened before, I'm skeptical but as supportive as possible)
He disclosed all his finances to me this evening which I did some crunching on. Given no credit debt, his monthly income is $400 over expenses. There's room to improve on ~$400 of those expenses: cable/internet/phone bill at a whopping rate ($200+) and cigarettes (yuck!).
Now with credit debt, minimum payments run about $900 a month, with most cards being in the 20-25%. As it stands, to be able to pay them down with minimum payments, he would need to completely cut out all unnecessary expenses (which again, I'm skeptical on). And of course minimum payments would take a few decades to pay down fully.

So I think my next steps are to do some more research into paying down unsecured debt on an extremely restricted budget, along with looking into debt consolodation options. Nothing else is coming to me right now since bankruptcy seems to be overkill and that 2nd mortgage is clearly a bad idea now that you all described it.