Not sure if you already checked on this, but Obamacare is ridiculously cheap after you turn 60. It can be much less if you're under 60, but there's more income hurdles to jump through. My wife retired about a month ago. Through her work we were paying about $1300 month for insurance. We looked at getting COBRA, but it would have been over $2,200 month. After calling an Obamacare agent, the agent worked out that we could get a plan with equal coverage for about $700/month. That's because my wife had income (worked) for half a year. Next year, I turn 60, she will not be working, and the same coverage will be about$325/month for BOTH of us.
I think when you turn 65, you are required to take Medicare, and are no longer eligible for Obamacare, but I'd recommend calling an Obamacare agent to find out.
Here's a link to get you started (if you haven't yet) -
https://localhelp.healthcare.gov/
BTW, not sure if you spoke with an investment counselor, but you may want to before you take social security. There's a few calculations involved in whether you take it at 65, or wait a couple years for larger payments, etc. Our financial dude calculated that I should take mine at 65, and my wife should take hers at 68.