First, a general comment on healthcare. Even the reddest of deep south red states has, yes, I know it’s shocking, but has one or more areas where you will find institutes of higher learning, cultural institutions, and high quality healthcare. Even Florida Man has multiple options for living where he can get a top-notch education, attend the symphony, and get high quality health care.
I am familiar with some of the places on your “currently considering” list.
For Florida, rather than Ocala, I would choose the Gainesville area (northwest-west-southwest Alachua County). Gainesville, IMO, has a lot more to offer than Ocala and you’re still close enough to Ocala to haul in to a show.
I will mention, though, that the company I retired from had several regional offices, including one in Corvallis, OR and one in Florida. 100% of the people from the Corvallis office loathed the weather in Florida on occasions when they were sent to the Florida office to work on various projects. The bitching, moaning, and whining was endless. The heat, the humidity, the relentless sunshine, they hated it all. Going from the Portland, OR area to Florida may be a tough adjustment weather-wise.
I don’t really care for the Raleigh-Durham-Chapel Hill, NC area. I used to live in Cary (west of Raleigh) and work in Research Triangle Park. The traffic is awful. I’m not sure 1.5 mil is enough to get what you want unless you go at least two counties out. The farm my kids took riding lessons at was in Apex and I believe it is now a subdivision.
I lived in the Lexington, KY area for quite a while and still have family there. I hate the weather; winter there is way too wintery for me, but it’s a great place to live if that isn’t an issue for you. The Louisville area is also nice. Like @clanter said, check out some of the communities east of Louisville. Really, that whole area between Louisville and Lexington is dotted with nice communities.
I like the Tryon, NC/Landrum, SC area. You shouldn’t have any trouble finding exactly what you’re looking for with a 1.5 mil budget.
My son and his wife live in Hawaii (Maui). She doesn’t love it, says it’s difficult to live there and the cost of living is oppressive, and she’s from Japan, so that’s really saying something. He loves it, but in their relationship, he’s the grasshopper and she’s the ant, so that’s not too surprising. 