I tried to go to college, wound up homeless, living in a van trying to pay for it. Now that I have a family, it just crushes me that I couldn't complete it.
That sounds awful. But the US is set up to fail people without money on pretty much every level, and that isn't your fault. Even if perhaps you happened to make some mistakes along the way, we all make mistakes... but some of us are lucky enough to have resources to help us get through the mistakes.
You're feeling responsible. That's good. Looks like all you need is moral support. For now, forget about college. Try to support yourself and your family. Hopefully things will fall into place. Good luck!
Moral support doesn't sound too bad haha. I have found meager wages working at a local repair shop, and have taken that time to hone my skillset into something useful. I have a firm handle on async Nodejs as a result, but it's hard to look at the applications I can make as useful when I struggle to put gas in the tank to get to the shop in the morning.
I'll get 99% of the way to 'completing' something, like the react-native app I am developing, and spend two weeks asking myself "Why don't you just watch Deep Space Nine on Netflix? It's not like anything is going to make paying rent this month any easier." and wind up like I am today, on the verge of tears instead of learning redux. From my perspective, I have been chasing a dream that will forever reward me with not-enough-money for my efforts.
Around here, at least, there are small one-to-three person shops that build websites for local companies, repair people's computers, things like that. And there's Geek Squad and equivalent jobs at bigger companies, that has a better hourly pay for some jobs it sounds like. Stuff like that.
By programmer standards they won't pay well, but likely more than $11/hour. And it's a start, and it sounds like you can obviously do some work.
So maybe instead of going straight for upgrading all the skills, start by trying to upgrade your pay by working for one of these? That way you get some benefit immediately, which might help with motivation.