I thoroughly enjoyed reading each and every post on this thread.
Here's some friendly and free advice that many of you probably already know, but in my opinion it is worth repeating if any of you don't already know it.
Concerning retirement, if your work at your job or business has become intolerable for you, then if you can afford to retire, I think retirement is probably a good choice for you.
If your work is not intolerable, then why not keep doing your work, keep making money and build your estate for your immediate needs (ie. more trains, etc.) and to leave a legacy for your spouse and children.
Concerning your various activities and interests, both before and after retirement, Voltaire in Candide had an expression, both literally and metaphorically, which is a great way to have a happy and productive life: cultivate your garden.
Literally, to cultivate your garden is a good and worthwhile thing to do if you like gardening.
I have a gangrene thumb, as does my wife, so we don't do any gardening. LOL.
Metaphorically, to cultivate your garden is, IMO, a great way to live.
What do I mean by metaphorically cultivating your garden?
I can answer that by explaining how it applies to me.
My metaphorical garden includes my law and mediation practice, my family, my trains and model railroad, an occasional golf game with my son, songwriting, singing and performing my original songs on guitar including doing so at Open Mics, watching baseball on television, talking to my friends (mostly fellow model railroaders), reading books, and reading and posting on this Forum. In essence, my garden is all of my interests.
To cultivate my garden means to continue doing my various interests and to endeavor to get better at doing them.
I can thank my parents, who passed away long ago, for paying for my Ivy League education at Columbia College. If I never got that education, I never would have read a book like Candide by Voltaire, and never heard of cultivating my garden.
To cultivate my garden has had a profoundly positive impact on my life, and I wish the same for every one of you.
Arnaldo