Freaking out what to do about bf in financial trouble!

Been dating the same guy almost 5 years. He had financial issues arising from his business failure over a decade ago (and he was convicted of check kiting). He was able to get employment until about 5 months ago when he was laid off. He's been trying but at 65 y/o, it's not easy. He is living off of unemployment and just inherited some money($50K) but it has to be left in trust and he already owes $10K to his credit card cos. He and I do love each other (a lot) BUT I'm freaked out b/c he wants to marry me as soon as he is employed again (and he reminds me he can also collect social security as of Jan 1).

I am a professional and a widow with 2 adult kids; one of which I'm totally supporting and another slightly supporting.
I am so torn up about this - I can't sleep through a night - i really don't want to break it off with my bf but don't see how I can marry him much less live with him. even if he gets a job, I don't trust his financial judgment and he has almost nothing saved for retirement.

What would you do???