In particular, I wonder how people set up their health insurance while on these epic bike tours. It makes sense that costs are minimal, you can have savings, etc. but insurance is usually tied to employment around here..
If your income has gone to/near zero in the US, you're immediately (next month) eligible for Medicaid. That gives you emergency coverage and if you're healthy enough for a long bike tour that might be sufficient. Getting prescriptions filled out of state could be a sticking point though.