35(f) asking about 35(m).

So I just met a guy who I'm interested in who is a recovering addict. He's been sober for 3 and a half years, though is still putting together certain pieces of his life that he damaged while drunk, like his finances.

My friends are really concerned that addicts, even recovering ones, don't know how to handle the hardest things in life like Houses, kids, and similar things.

Any advice out there on red flags to look for, questions to ask to try to get an idea on what might be too much for him or just other things to expect when dating someone like this?

I'm very hopeful, and want to make sure I set us up for success if things continue in a positive direction....