You paint a realistic picture. However, based on Houseland, I have confidence that House would land on his feet. Sadly, House's survival might be made easier if Wilson were to die. Wilson would probably put all his money in a joint account that House could could access. Perhaps after Wilson's death House would take on Wilson's identity and return to medicine. If not, House is intelligent and knowledgeable. I should think he'd find a shady individual who would provide a new identity. Then House could find a way to earn money. I don't get the impression he lived or required a lavish lifestyle. As for health insurance, there are free clinics. If Wilson survived, I'm sure he would earn enough for both of them.

I hope I don't come across as trivializing your concerns. I just want to cheer you up by offering alternatives--fictional and in real life. It's amazing what people can accomplish if they have ambition. There was a family friend who became a millionaire during a downturn in the economy. He collected rags, cotton rags and sold them as industrial cloths. Cotton had become a scarce commodity when synthetic fabrics became popular. You don't need to be a genius or even a degree to come up with that idea. Building a financial empire might even be a puzzle House would enjoy. Or take my uncle--please! He barely worked a day in his life, but found himself a wealthy woman to marry.