Accountable wrote: My brother is out of work, out of luck, and generally out of his mind. He has substance abuse issues that keep him from holding down a job, and now he is several months behind on his mortgage. Should I help?

“How can you even ask such a question?†I can hear the question you ask. Yes, he’s my brother. Yes, he needs my help. And even though I am currently unemployed, I could probably afford to give him one or two months’ payments so he can keep his house. But is that helping, or just delaying the inevitable? :-5
None of us are young. I’m in my 40’s and am the baby of the family. My brother – let’s call him Tad because it sounds preppy – is in his late 40’s and is single. His house is a shack that would have blown down long ago if the neighboring trees hadn’t blocked the wind. I can’t help but feel that giving him money would do nothing to improve his life. He would not be able to take advantage of an opportunity because of it. He would only be able to maintain status quo for a little longer.
Am I a stingy putz? I’d appreciate disinterested feedback.
Brother or not, at his age he has chosen to follow his life's path on his own, without your help. You mentioned that you are unemployed yourself, so money may eventually become short for you also. So you need to worry about taking care of yourself, as no one else is going to. "His Shack" is not worth saving from what you said, so why should you spend your money for him to keep it for another month? It sounds like Rehab house is the place where he should live.
It would be the best place for the both of you! (Just my disinterested opinion)