Thank gosh for the internet. It saves lives for sure.
That said, without prying into your IP or anything, where do you live that you cannot get health insurance? My credit is bad mostly because of healthcare, but as of pretty recently, even in the states I can get coverage for most serious problems. My teeth are bad I'll admit, and the only dentists I can find who take government insurance are either inexperienced or are war veterans who don't speak english very well, but still. I don't have to budget for drilling these days, and I don't get calls at 6am or 8pm about recent medical costs anymore, just about old ones.
I have never made 9.88 an hour except under the table. Even with dependents you should be able to pay rent with that in most countries and also pay for electricity and your phone and internet. That's a lot of money. If you can't support your boyfriend on that pay, maybe he needs to go figure himself out and come back when he's more stable.
I'm generally in the camp of giving people the benefit of the doubt, of helping those who are going through stuff, of being as kind and generous as possible, but it sounds like you are doing way too much to try to take care of this guy you are dating. Even if he fails and has to sleep outside, that might be for the best if it's the way you stay sane or become healthier. If he thinks being outside or without loved ones is the end of the world, maybe he just needs a sleeping bag or a teddy bear or some Sartre or something.
People are here for you. It is not on you to save this man you (may or may not) love, but it is on you to save yourself. Don't feel bad about whatever steps you need to take.
