I had been on cobra after I retired. I turned 65 a few months ago, so I am on medicare. My wife won't qualified for medicare for 4 more years. We factored in the cost of health insurance when decided to retire. It is expensive, but within our budget. I have chosen to go with medigap rather than medicare advantage, so I don't get eye or dental insurance through it. Not losing either insurance until end of december, haven't decided whether I am going to get outside insurance for them. Went with Medigap because we are not sure if we are going to become snowbird and have a place in Maine. Medicare advantage is tied to a state where medigap is nationwide.
I was a CPA and my wife was in the financial industry, so we are pretty conversant in finance.
Initially we took are spending for the last 5 years (I track every penny, I know obsessive). Used a 4% inflation rate and added in extensive traveling for the first 2 years of retirement. We then took our current asset used a 4% annual yield. Then just ran it out. Once my wife was convinced by this we would not run out of money we retired.
Reality at the moment we are earning more than 4%, in fact after 2 years we have more assets than when we started, in spite of all the travel we have done.
We have a pretty mixed portfolio, some individual stocks, mostly ETFs and then treasuries. We rebalance about every 6 months (generally when it looks out of the balance we want by a significant margin).
The big thing about retirement is not the money, but the ability to do things. We have been on 14 cruises in the last 24 months and you wouldn't believe what you see. There are people who just can't get around, walkers, scooters, etc. I don't see how they can be enjoying themselves when they can't do anything. My wife's late husband died when he was 59 and they had all these plans that they didn't do. We decided we would sooner run out of money doing thing while we can than wait to make sure we won't run out. Robert Herrick said it well "gather thee rosebuds will ye may"