> 2) When choosing my next job, what job/career alternatives should I consider, assuming I don't have the resources to try to build another bootstrapped startup right now? I'm ok taking some risk if necessary but not "you might work for two years and end up with nothing" level of risk.

What's your side project? (Can you describe it in general terms without specifically identifying it?) How well might it align with an existing company? Can you think of a company that would pay you to work on it, either full-time or as a major component of your job? Have an off-the-record conversation with people associated with that project who work elsewhere; see if someone might hire you. (Consider both the "doing it as a paid project" angle and the "Open Source it and get a paycheck to work on it" angle.)

If your side project is something people want, getting a medium or large company to pay you to work on it seems entirely plausible.