Wow, sounds like you've got a lot of challenges. It's tough when you turn to someone for a shoulder to lean on and a benevolent ear and you end up getting back judgment and/or "advice" that undermines your comfort and confidence. I can't imagine being uprooted and essentially homeless. I hope you find some affordable housing soon!
I've got a 17yo and a 14yo (as well as a 12yo and an 8yo). My eldest goes to school part-time in order to use the local school's independent study lab and its courseware. She's an achiever -- always on her own terms, but an achiever nonetheless, and I've learned to mostly just get out of her way. She's got a lovely future mapped out for herself and I don't really have those "not learning anything" panic attacks about her. I did when she was 10/11/12/13, but she's been very driven since about age 14.
My 14yo is a boy and he spends more time on the computer than I'd like. Sometimes I worry about whether he's learning much. He plays viola, and sings tenor in a fabulous choir, and does amazing things on the computer ... but sometimes there's not much else. He is a perfectionist and an introvert and has a fair bit of achievement anxiety (meaning when he's in a situation where he or others are hoping/expecting him to accomplish something specific, he tends to get very anxious and shuts down or bails on whatever it is). We've gradually come to realize that he does need a bit of pushing / active support to get him to stick with things when they first become challenging. For instance this year he decided to do some formal study in math and science and signed up for 10th grade academic courses in those areas through the local homeschool program. He started out okay but when it came to doing quizzes and assignments he had trouble working through his anxiety and developed a distaste for these looming requirements. He put them off, and off, and off, stalled about 10% of the way through his courses.
Over the past two weeks with his blessing we've sat down together for an hour or so a day to go over his coursework -- reviewing, organizing, discussing, moving ahead -- and he's finally feeling confident again, having got past a few hurdles. He wrote the math midterm on Thursday and totally aced it!
We talk about all this stuff, including what role he would like me to play in structuring his learning, in "learning conversations" that we hold every month or two, beginning with a major one in the late summer or early fall. We, too, are bound by some academic requirements, and that's where we collaboratively figure out ways of coping with those, as well as brainstorming our way through learning interests, resources and supports that the kids want to develop or procure. It really helps us feel like we're on the same side when it comes to dealing with 'requirements' or to living happily together and trying to prepare for the future. I don't know if this idea would be helpful for you and your ds.