dunno if you're still considering applying, but to be honest you already meet the minimum requirements for applying, which is at least a B in one college-level/non AP Calculus course. You have what sounds like a pretty good blend of work experience, and the application process is holistic, so I think you would have a good chance of getting in especially if you have already taken quite a bit of advanced/upper division math, and a bunch of programming experience. You might have to take some classes over (possibly physics)
Financial aid honestly sucks; theres a scholarship offered to LEAP students for Phase I but not all students get it. There are 2 federal loans available to all LEAP students, the direct loan and the PLUS loan which have a combined yearly total of ~82k. In terms of adjusting/moving to Boston and the chances of getting financial aid, the best semester to apply for is Fall
Alternatively, inquire other universities about possibly being accepted for a masters program; you have some probability and stats classes, and if theyre calculus based, it's to your benefit. Contrary to what people might think there are quite a bit of universities that accept engineering masters students who dont have BS's in engineering. They will instead assess what classes you have taken based on what they consider to be "baseline/essential" courses for all masters students; whatever classes you havent taken, you might be a provisional grad student and have to make up deficiencies once you get accepted.
hope this helps