Clayton,
The insurance companies are far from blameless in this. They can and do cancel policies just because your costs have gone too high. They call this “recision” and recently insurance heads, before congress, testified that they would not forego that practice.
Furthermore, I see no way in which the private system will cover people (like myself) with pre-existing conditions – except by excluding all risk from those conditions. The insurance companies have to fear adverse selection (which is what doomed the Mass. experiment) – where people only buy insurance when they get sick or have an expensive procedure to do. As long as the young can choose not to buy coverage, the old and sick will not be able to buy coverage. Generational transfer is necessary for the system to work – think of it as the modern, anonymous version of grown kids taking care of their ailing parents.
As for your resume, there’s a couple of problems:
All the non-work related stuff (which is quite remarkable and commendable) is likely to scare a lot of hirers.
And, of course, you don’t have any experience in FORTH! 
