I'll share my thoughts for what they are worth.

Never "not" try for something because someone tells you that you can't. Looking at the figures you've posted he won't qualify for Medicaid, but that doesn't mean you shouldn't try. Generally the representatives will even help you try to qualify and give you pointers on how do it, they are the experts you know. Get the facts from the source not from "other" people as generally people don't have all the facts and speak out of ignorance. Just ask me I'm the most ignorant person I know

As far as everything else...take it one step at a time and breath, don't let it overwhelm you. What I found is that there is always a way if you look for it.

Bon Chance!

Eric