What I hope happens is when I turn 62:
I have enough to retire, but I don't. I tell my boss I'm going to work 100% remote. No more coming into the office. I strictly manage my aftermarket sales. In fact I want 2 extra weeks off a year. Unpaid of course. I work 9am to 4pm not 8-5pm.
Those extra 2 weeks, I use to spend 3 weeks in Greece every summer. Most all my other vacation days are used for hunting season.
January 2nd drive from MI to Florida and work from Florida from then till April. That's 4 months in Florida. Work from Florida. Off at 4pm. Walking the dog on the beach at 5pm till dark.
Drive back to Metro Detroit in April and get ready for summer on the lake. I live on a lake so summer is like vacation every night right in my back yard. 6 months in Metro Detroit
October 1-Jan 1 is hunting season. Spend a lot of time hunting.
I would be bored if I didn't have a job. Even if you have plans this weekend with friends who work, you spend all week doing nothing pretty much waiting around for the weekend to come. Even if you had unlimited money, what would you be out doing right now? Nothing. Same thing you're doing now. So yea, I'd rather keep my job if I can cut down the hours and get a few more weeks of vacation.
Secret. I would even take a big salary cut in exchange for all this. But I won't tell the boss. I'll just see if he keeps my salary/commissions the same as long as my sales don't suffer why not? He should be scared I'll quit. I'll let him know I don't need the job.
Don't kid yourself. Once not working, you ask yourself "how did I get all this shit done while I was working!"
I'm always busy although I admit it does get dull in the winter. In the summer, there doesn't seem to be enough hours in the day. When you don't work you go to sleep later and wake up later. You're not rushing to get ready for work. You come here for a couple of hours, watch the news on television, make a nice breakfast, and eat in relaxation, maybe grab a shower.
My situation is that I own rental property, and there is always something to do here, especially when you have a large yard. My mother never drove a car in her life and needs rides to places all the time. Dad can take her, but I like to keep him off the road as much as possible. Pop is 91 now and his driving skills lack. Even he knows it.
I used to hit the grocery store on the way home from work. Now I call my mother, we go shopping on a Wednesday about 9:30 am since the store is so much less crowded. By the time I pick her up, go shopping, take her home, help her unload her groceries, go home and unload mine, that's around three hours right there, and that's if she doesn't have to go to the bank or Walgreens to pick up her cigarettes.
The considerations you have to figure in is not only if you can afford to retire at 62, but what about ten years from now? Sure, you can work part-time now, but will you be able to do that later on in life? As you stated earlier, healthcare costs are something to consider. Do you really want to retire, and if you're going to retire and not sure if it's really what you want, can you go back to work full-time and get off of retirement by SS standards? That I don't know.
What about if you work until 67, will you still have your health by then and afterwards? What enjoyment will you get from retirement when you can barely make it to the bathroom in your own home? In my case I was forced out of work at the age of 59. When I turned 61 last year, I learned I was full of cancer. They gave me six months to a year with no chemo. With chemo, they may extend it by months or a couple of years. Who knows? Now if I was working until I became this ill, I would have likely been working until the day I die.
Retiring is simply not working, it's gambling. There is no way out of it like there is no way to foresee the future.