Thanks, everyone, for the support.
Yes the $300K rental (single family) is now worth $400K and I'm finally getting better rent - $2300 month (but could maybe get $2500 or more if the tenant moves out and I do some work). Worried about recaptured depreciation and capital gains if I sell but maybe not enough to move in it --- will have to try to figure out how much the taxes would be (paid $92K about 30 years ago).
Was about to do about $40K worth of work on my own house. Pondering that now. There is a guest house out back and I could move back there and get maybe $2500 for the main house.
So, fast-forwarding past five years, you have now transitioned into a new career: "real estate investor" ("full-" or" part-time," whatever you decide) and/or "semi-retired" (since you can probably live off your real estate). Because of your smart investments, LBYM, and overall frugality, you are now in a position many 50-somethings would envy.
The world is wide open, and you are now your own boss. Enjoy!