John, what if you were to move to more reimbursement style shops to keep your income down? Could that allow you to do both? Can you get groceries, oil changes, car washes, etc. paid for through mystery shopping so it wouldn't add to your tax burden but would defray your everyday expenses?
I agree with others above though, it seems like it wouldn't make sense to give up $2k to save $185. I haven't seen them in a while but weren't there some shops that were actually about the different Medicare plans and their pros and cons?
I get my insurance through ACA so I'm not familiar with this at all. Just trying to send out some thoughts for you to mull over.