Ive moved around heaps in my life, the RAAF along with my hypo life - countless moves, maybe 30?
Im still met with the trepidation you mention. In fact we are selling up now and moving for the last time which might interest you.
I'd be hesitant in choosing a retirement home. They sound great but reality might not match up and then you're stuck.
Two other options.
First, a country town. Ibe lived in a town of 200 with a shop as the only facility. Not good. Relying on a car, 22km from the nearest small town of 4000 which is the perfect size, all facilities including medical, hospital etc. As soon as a town goes over 15,000 population it loses its intimacy.
Or rent in the same size of town.
Better if a railway line is in the town. Also over 170km from the large city or you'll have city commuters and sadly they often dont blend with country life and sometimes return to the city.
Our decision is to buy a block of land, 30 minutes from the beach, inland as its cheaper, 2 hours drive to the city, 4000 population, 24 hour emergency at a hospital, 2 large supermarkets and build a transportable new home on a small low maintenance block (less than 600 square metres at around $60,000.)
So anxiety will rise but settle after a few weeks.
All the best