I don't know if I can tell you what you want to know, but I'll tell you what I did. Before retiring, I paid all my debts, including my house and all but one car. I have a steady, reasonably comfortable retirement income and health insurance. My son is still in college, but I have enough savings to pay his tuition and fees. He's working to pay his own room and board. My boat isn't new, but it's nice and it's paid for. In short, while I'm not flush with money, I'm comfortable and financially independent. That's important, because any financial limitations limit your options, and your ability to absorb unexpected problems.
I keep my boat on the Chesapeake, live aboard it during the summer, and was new to the area, so I didn't know anyone at first. I began looking for opportunities to crew on other peoples' boats in Wednesday evening and weekend races, and now have a lot of friends in the area, and ample opportunities to socialize.
I have all my mail forwarded during the summer to my Maryland PO Box, and virtually all of my regularly recurring bills are paid electronically. I have a cellphone, so I can be contacted during the summer, in the event of a family emergency.
When you first move to a good sized boat, you'll have to learn a little seamanship, to get the boat in and out of its slip. If you singlehand a lot, that will make it more difficult, but you can learn to do it with practice.
The biggest concern I have is that, as you age, your leg strength begins to fade, as well as your balance. You can reduce that with exercise, but you really need to start using jacklines and safety harnesses when you leave the cockpit, even in calm seas, because one misstep can leave you treading water, watching the boat sail on without you.
I occasionally have old friends and relatives visit me for a few days and stay on the boat, and have found retirement to be as fun and as satisfying as I had hoped. My only regret is that, so far, I have had to spend the winter living in a house, but, now that I have most of the repairs and upgrades done on the boat, perhaps I'll take the boat south for the winter.