A health insurance premium of $1K a month sounds reasonable to me, based on your advancing age, since you also mentioned SS benefits. Your job sounds like it's played out for any number of reasons - some you may not be aware. It's a shame it's come down to the health insurance premium amount driving your employment focus, but you're certainly not alone in that boat. You've got a lot of company in that pursuit right now.

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'06 E320 CDI
'17 Corvette Stingray Vert