The need for health insurance has kept me working far longer than I really wanted or needed to. My BIL is a year older than me and asked for a layoff and bought COBRA coverage 18 months out from his Medicare eligibility in March. He said it cost him about 8k out of pocket and was worth every cent.
A few years ago I wasn't planning on letting health insurance keep me from retiring, as my wife had good coverage as well (I was going to sign-up on her plan). But then she took a new job, and their health insurance sucks....
As for the BIL, 18 months I could see....But I just turned 60, so I have 5 years before I can sign-up for Medicare!