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Because of my own life experiences, my first instinct is to say don't trust him, he's just milking you. People don't often wind up in jail for no reason. People whose lives devolve to broken marriages, jail time, poverty, etc, usually bring them on themselves in some ways, and they are often the best at spinning yarns to make others feel they are innocent, so that they can milk these poor saps for all they are worth, until they finally say "no more!"
But as I said, that's my experiences, with an alcoholic sister and a deceased brother you wouldn't believe if I described him to you. And btw, he made a living, literally, by getting people to believe he was a nice guy wrongly accused of crimes, and whose wife had left him because of health issues, and much of the rest of what you say, so I'm even more inclined to not trust this person you speak of. Many a kindly person found themselves robbed, raped, and no telling what else because they beleived this very convincing man. I'll never forget the time our preacher took him in, even chastising us, indirectly, ina sermon for giving up on this man who was so obviously a good man, so obviously trying to change his life, so obviously just an unfortunate victim of bad decisions and an inferior brain that put him in these situations. After my brother stole the chruch soundsystem and sold it for drugs, the preacher apologized to us. My brother died of an OD (and believe me, that was a good thing), or I'd ask to make sure he's not the one you're describing, since I heard him described exactly that way and in that tone so many times.
But as I said, that's just my instinct, based on my experiences. I have met people who are truly down on their luck, so I know they exist. Maybe you have one of them. If so, you should be proud of helping him, and I believe that you should do as much as you can for him, until you either a) find out it is hurting your own family or others who rely on you too much, or b) that you are enabling him. Even good people will take the easiest way at times. Are you helping him, or are you delaying his having to face reality? You need to ask whether anything you are doing is going to put him in a better position at some point in the near future (say, when his disease heals or stabilizes), or whether you are just keeping him afloat until you finally cut him off. If he won't be in any better shape next month or next year, then you aren't helping him, you are raising him. Better to cut him loose. If you are helping him until he gets back on his feet, and you see a clear path for him to do so, then keep it up as long as you can.
ANd if you think you are doing the latter, but notice that somehow all of his decisions and everything he does puts him right back where he was to start with, then you really aren't helping him, and you really do need to analyze whether maybe he's conning you--maybe not on purpose or with evil intentions, but still conning you about whether he's trying to move on, or just trying to take the easy way while you support him.
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