High demand specialty jobs that might help pay for the schooling?

Some nursing schools that are part of hospitals will pay for the schooling in return for a commitment to work at the hospital for a certain length of time after graduation. The University of Texas at Austin has a software developer training program that pays students a salary to learn to maintain the university's legacy mainframe database systems, and there is a commitment to work for the university for a period of time after receiving the training. Google "UT Austin Software Developer Training."

A lot of hospitals will pay for people to get nursing degrees. It helps to be some kind of clinical employee already, and you always have a multi-year commitment afterwards, but it's out there. This is changing though. A lot of hospitals and health care providers in general are starting to hunker down, as there's widespread anticipation that Medicare/Medicaid benefits are going to be cut significantly in the next few years. As this is pretty much the only way we're going to balance the federal budget, it's not an idle fear. Private insurers are also in trouble, as the new health care law has created some uncertainty there. So there's far less hiring going on now than there was five years ago. Outside health care, most of the training programs of which I'm aware are either generalized educational benefits provided by employers, i.e. if you're already an employee they'll pay for a bachelor's, or they're specialized educational benefits targeted at advanced degrees, e.g. you've got a B.Eng., but they'll pay for an M.Eng. That one is actually fairly common. But if you're looking for jobs that take people more-or-less off the street and train them up, dpx.mfx has it: trade unions are actually hurting for workers in a lot of places. I'm talking plumbers, electricians, glaziers, painters, you name it. Most trade unions have apprenticeship programs, and many are hiring.

Ask the technical colleges or community colleges or public university near you what they offer.

When my mom was promoted to management in the state psychiatric hospital she worked, they paid (as in, full tuition plus stipend) for her to get a MSW in Rehabilitation Therapy. This was about ten years ago, however. Before that, the only degree she had was the Soviet equivalent of a BFA in Fine Art. Unfortunately, regardless of the demand of jobs like that, hiring freezes are making things difficult.

Some of the trades and crafts will do this - think electrician, cement mason - although I doubt it would lead to a degree. Check your local union/hiring hall.

Based on what I've read on the internet (so take it with a grain of salt), if you can pass the first two actuarial exams on your own, insurance companies will hire you and help you pass the next four exams. After 6 exams, you become a real, licensed actuary.

Doing a PhD gives you lots of specialized training, and (at least in the sciences) is almost always subsidized in part if not in full. While it is certainly frowned upon, a lot of people start a PhD, get a few years of training without spiraling into debt, and then leave for industry without finishing the degree.

If you are willing to teach special Ed in an urban area, there are programs that will let you get paid to teach while earning your teaching cert.

Depends where you are. Near me, I'd say mining.