I agree, I don't see myself ever retiring completely, although I may or may not be involved in a money making endeavor. Most likely I'll just continue to see some favorite patients very part time, or write about medicine in some way.
My mom is a good/inspiring example. She was widowed in her 30's with 4 kids, then divorced after ten years in an unhappy second marriage. Unfortunately our home appreciated a lot during that second marriage and she had to sell because in our community property state he was entitled to half of that appreciation. She moved into an inexpensive apartment type condo that my brother and I helped fix up (that was my first kitchen tile backsplash!). She moved from bookkeeping to becoming a CPA (taking and passing all 4 parts of the CPA exam on the first try, almost unheard of!) and worked as a (relatively low paid - hello age discrimination!) tax accountant until her retirement. In the meantime she moved to a more spacious single level townhouse which my siblings and I also put some sweat equity into. She acquired a very modest retirement account while working as a CPA.
When she retired, she moved to my city and my ex and I helped her buy a house there. We helped with half the down payment and some serious sweat equity remodeling (we installed a whole new kitchen ourselves from Ikea flat pack cabinets, for instance) and she made the payments.
What really made the difference for her in retirement though was that she started volunteering at the library, and was eventually encouraged to apply for a job there. She worked part-time (20 hours a week) until she was about 85. She loved the work and the socialization. And the extra money kept her comfortable and funded low-budget international travel that she took me and my sister on.
The lesson from that all is that even a small part-time income in retirement (preferably doing something you love!) can buffer you from inflation and keep you young and active. Not all will be blessed with her good health but even a hobby may be a source of a little extra money in retirement.
Bttrfly - once you get things worked out with the houses - whether you rent or sell - you'll be in a good place. And those financial skills you honed keeping the household budget down will stand you in good stead.