You were homeless and didn't have a choice, so now obviously you're qualified to give assurances that essentially, "it is unlikely that your family will starve", right? /s

And if you're wrong, and shit hits the fan for whatever reason, who's going to fix that? You? No, he's going to have to fix that, because nobody else is going to step in.

It's easy to tell others that it's going to be OK, but put your money where your mouth is. Put $1M in a fund that he can access should he no longer be able to find employment. Then he'll have absolute certainty that it's going to be OK.

Something tells me you're not going to do that. Something tells me that what you would do if shit hits the fan, is you're going to tell him that he should find solace in the fact that while he's working for 1/5th of his former total comp, putting in more hours at the same time, seeing his kids less, not putting his kids through private school to give them the best chance at the best education, that, at least, some kid out there isn't watching 6-7 videos on the tablet that their parents use to do less parenting.