I've lived in a cohousing community since the mid 90s. Our original intent was to have an old-timey neighborhood, safe for swarms of kids. Great place to live! However, we own our land (owned in common; we're set up as a condo that we all own rather than a co-op, which fits better, as banks here were hesitant to write mortgages for co-ops back then).

The notion of a tiny home community sounds lovely, but I’ve been watching corporations (mostly owning REITs) buy up trailer parks, then jack up land rents to extract as much profit as possible (most trailers, in spite of the name, are not readily transported — so the owners can’t vote with their feet). I’d look very carefully at landownership arrangements before deciding on a site.

Also, as this is about retirement, all of the tiny homes I’ve seen have the bed in a loft or at least with some kind of stairs between bed and sanitary facilities. Not ideal for anyone who needs to get up in the middle of the night. I’d suggest giving one a try before you commit — I’ve seen a number listed on AirBnB (and there are probably more on similar platforms).