I am a wandering hacker, as you describe. Many years ago I joined the Air National Guard (part time -- one weekend a month, two weeks a year). They offer a very good health insurance program for less than $60/month. You read that right! It's pretty unbelievable, and is one of the reasons I stay in. It is subsidized by the taxpayer, of course, so I really do thank all of you. Some people say that not many doctors accept the plan (called Tricare), but I live near a university hospital, and I've had no trouble at all with them taking it. Physical therapists took it, too. The cost for a family is around $250/month, and the dental plan is $12/month.
The Guard is now getting into cyber work. I am not part of that, but you might want to check it out. The Guard has been one of the best things I've ever done. I have made great friends, and it's never really interfered with my civilian career.
The steady state commitment is "one weekend a month, two weeks a year." There are, however, boundary value and perturbation exceptions, i.e.:
(1) At the beginning of your service, you will have to go to either basic training or officer training school. For heaven's sake, be an officer: pay is better and life is better. This school is several weeks long, and is full time. (2) If there is a national or local emergency, you could be on the hook to be asked or ordered to serve. In my experience, this occurs about once every 10 years. Balancing these demands on your time, however, are: (a) When times are lean in the civilian world, you can usually find openings to get put on orders and get some income, (b) I have made fantastic lifelong friends in the Guard, which rarely happens in the civilian workplace, (c) a great pension plan if you stay in 20 years. There are Guard recruiters in every town. If I were you, I'd look at cyber opportunities. It is one of the few areas in the military where spending is going to go up.
The Guard is now getting into cyber work. I am not part of that, but you might want to check it out. The Guard has been one of the best things I've ever done. I have made great friends, and it's never really interfered with my civilian career.