Thanks Jersey Joe and as always Zambonir, I am really looking for my future near-retired job.
My reason for looking at Uber is really the insurance possibility. I realized that if I do 20 trips I can become Uber+, at which point I can buy health insurance through them as long as long as I do 1 trip/month. The Gold rated insurance for a couple is $500/ month and is ok insurance ($35 visits, $6K deductible, $15K max per year, drugs costs somewhat covered). That isn’t great insurance, but I is better and cheaper than on the open market.
Honestly, my first choice for semi-retirement would be to go live in Europe for a few years, but I will NEVER talk my wife into that.