Any regrets for those opting early retirement... other than waiting too long?
A lot of my friends are retired... most are career military or public safety. As one told me, he was basically working for a couple of bucks an hour as an Oakland Police Officer as his pension with medical was 90% of his pay... so at 53 he retired with 30 years in... spends most of his time being there for his grandkids as he missed a lot when his two were young...
I can see where those with a nice pension might have an easier choice.
This week has been a wake up call... tonight two of my co-workers were in tears... they have more time in than I do and their positions are being eliminated as all accounts payable and receivable will no longer be onsite... both have been offered positions in admitting and medical records and are willing to give it a try but it is very much like starting over.
Some here have said it should be looked at as starting a new job... and that is very true.
I retired at 61.5 and have no regrets at all. I realized I was selling my days to the company for less than they were worth to me. Especially when I thought about not knowing how many days I had left. I am coming up on the 10 year anniversary of that in a few months and it has been a great ride. Plus, it looks like the ride will continue, since my health is good.
Now, I have a company pension, DW kept working, and the finances were easy.
Your situation is different because of the lack of a pension. OTOH your rentals are a great asset.
At 57 and no company retirement, frozen over 10 years ago, not sure I would be out looking to hire on.
Thankfully, I have kept a small portfolio of rentals which are now all paid for... so it is not a question of putting food on the table... my needs are really very modest.
With your background of building and facilities management/maintenance, and your personal history of successfully owning and operating rental property, you should be planning for a new employer -- yourself.
Look on this as the opportunity of a lifetime. I call myself retired now, just because people understand that, but at the time I was doing it I thought of it differently. I made the decision that I was going to "declare myself independently wealthy." Now that I have had some time to think it over, what I was really doing was becoming comfortably self-employed.
We did section 1031 exchanges to sell our rentals in the SF Bay area and buy new ones in our retirement location. You can do the same thing. Do not be afraid of mortgages in "retirement," as long as they are for money-making assets they are a sound and responsible financial tool. Your tenants will end up paying them for you. Buy multi family rentals, maintain and manage them yourself, and you will be in great shape.
It is going to be easier to get loans on new properties if you are employed in a traditional job, so don't leave until you have your new self-employment/independent situation set up. But, one of the beauties of real estate mortgages is that they can not be called if your situation changes, as long as you keep the payments up.
If you want to discuss some details off line, send me a PM. With 20/20 hindsight, my only real regret is that I did not buy more rental units.
I could put up with a lot of BS at work if I had a solid plan for a very comfortable escape in a year or so...