You’re in rural Indiana and worried about the job prospects. But you got a job at a YC company before. How did you do that? Can you run that same playbook now to find something?
> How can I justify the high cost of COBRA health insurance with limited funds, so my high school teacher wife isn't burdened by my potential medical debt while being our sole provider? How do I fall asleep at night?
Instead of doing COBRA can you get on your wife’s health insurance plan? It’ll almost certainly be cheaper than COBRA and a spouse’s job loss should be a qualifying event to let you enroll mid year.
If not remember that you can enroll in COBRA retroactively for some period of time. If you get something lined up soon might be worth it to go that route.
Best of luck!