PC game market seems tough, practically impossible for a lone developer to crack it (although I have noticed exceptions). Tapping a niche market would be vital but also easy to mis-judge.
Recently discovered a game called Amnesia - the Dark Descent made by a small team of Swedish developers without a publisher. It received very positive reviews and created a lot of online buzz due to its capacity to frighten players - like, much worse than horror films usually manage to. Nevertheless I read on the developer's blog that sales have been disappointing so far. That must be crushing after the enormous amount of work that went into it.
Mobile device games seem the quicker and less risky route.
Re: jobs and bills, my circumstances are good, relatively speaking. I can afford to take risks and am comfortable with very frugal standards of living when necessary. My partner is the same. Even with the global economy so unstable Canada's IT industry has remained robust thus far. There is room for someone like me to maneuver.
Re: programming classes, who has the time & money for that nowadays?

Relying on dev books, online lectures and practical experimentation should be enough, surely?
Hatonastick, when it comes to working from home this does seem a way to do it. IT related stuff in general can lend itself to that kind of arrangement. I used to run a small Web Design business from home as a sole-trader and found it satisfying. It was much harder work than being employed by someone else but was also less stressful (in some ways).