I can easily flip this argument around and say that you're actively trying to slow down a disaster, especially now while DSP can't use any credit lines and relies solely on cash. I'm not using the word obsessed, but I could have easily done so, looking at the fact you sent him literally thousands of dollars in the past, helping him keeping his head above water.
Also: IF the bankruptcy goes through as intended and/or MidFirst Bank somehow won't succeed in what they're trying to do, there is still a possibility he doesn't have to pay off his credit card debts and/or the remaining CT condo mortgage. So by throwing cash funds his way, you're kinda gambling on that being not the case, which is a risky thing to do within the DSP Universe.
No one is telling you what to do or what not to do with your money, but I think the "Don't get directly (financially) involved with DSP" standpoint is a wholesome and wise one. A bit too late for you, I realize that, but for what it's worth.
