One of the things that worries me is not knowing what the resale market will look like in the next 20 years. If I have to sell my SSR will anyone even want to buy it? Maybe I'm overthinking it.
PS - you folks with 800+ pts talking about retirement scares the crap out of me, the dues on those points keeps me up at night right now and I can't even imagine it when I'm in retirement. That's not an insignificant amount of money per year when I have no income.
Pre retirement fears hit most of us at some point in time. I retired in 2021 I was 64. I also thought I wouldn't be able to afford my life once retired, and I wanted to do more than just sit home. My marriage broke up at age 55, so I basically started over then, buying a condo, helping my son through university, and being frugal so I could afford to keep my contracts (small contracts totalling 200) and still go to WDW once a year.
Long story shortened-at some point you make some tough lifestyle choices. I wanted to travel, so I sold my condo, invested the money. I couldn't imagine not owning my own home, but it's turned out okay. My investments supplement my pension income, and I've been to Paris, London, Rome, Venice and most recently Amsterdam. I'm still not a big spender, I rarely eat out, drive an old car, hope it holds a few more years

I did what Brian Noble suggested, I got a fee for service financial planner who looked at my investments and gave me a cash flow projection, net worth projections, and a clear plan of where my money will come from up to the age of 95. I had anxiety about hiring him, but I sucked up my courage and did it anyway. Turns out I'm better off than I thought. I'd have been even better off if I'd paid attention and got this done when I was first on my own, but hindsight is always 20/20. I hope you can figure it out. Lying awake at night worrying will kill your joy faster than almost anything. Good luck.
That long story didn't really get shortened, did it.
ETA: BTW I'm not rich by any stretch of the imagination, but I have enough. Give some thought to your concept of enough.