I'm off track. I was hoping to retire last year but was unable to pay off the house due to settling my roommate's estate, I had to close his IRA to distribute funds to family and took a $32k tax hit, which I have overcome but had to refinance his house in my name instead of paying it off. The good news is the estate is settled so I'm done with that, and my house payment is only $600/month despite the 6.5% interest rate.
My company wanted me to stay longer so they gave me a new, less stressful job. They want me there for 5 more years but I will probably be done in 1-2 years. In 2 years I'll be 58 so I'll do the rule of 55 and draw off my 401k for any major unforeseen expenses that cash can't cover until I reach 62. For medical I don't need COBRA now, I'm planning on using VA, just have to get ACA until I'm off the VA waiting list. I also have funds in my HSA.
My property values continue to rise, the 3 properties are at almost a million in value. The plan now is to snowbird, sell the main house, sell the beach house, develop hookups for my paid acreage next to the beach house, and camp there during the summer in a travel trailer with a small shop/garage for more room. This will also keep taxes low and it's still 5 minutes to the beach. Then retreat to a winter condo in Florida or Texas.
I go back and forth on paying taxes and HOA for a condo, but on the other hand I'd have to pay taxes on a home and I won't have to deal with yardwork, pests, maintenance etc., just paddle my kayak, fish, volunteer, and play pinball. In fact most HOAs + property taxes are around $1100-$1200, cheaper than an apartment. I'll buy with proceeds from the house and beach house sales and be debt free with a ton of equity. Plus I can have someone run my condo as an airbnb or Vacasa while I'm not there during the summer if I want more money, just have to buy in a place that's not 55+ only.