[villagetinker]

We got very lucky, when we bought (2013) we were at the southern end of the villages between 466a and 44, we did not look at other neighborhoods just looked at house designs. We found a design we liked and then found a lot and had our house built for us. I understand this is no longer an option. In any case we ended up with great neighbors and we are just North of the center of TV. We did like the layout of the area.
OP, your points are well taken. As for your wife, health care could be better, if you move before she turns 65 she will need to find suitable coverage, and you might want to start looking early. Also, be very careful about traditional Medicare and Medicare Advantage there is an organization SHINE (Senior Health Infromation Network) SHINE - Home that provides unbiased information, that saved us from making a big mistake.
There are some areas that some people regard as less desirable but this is a matter of opinion. I am sure you can find an area you will like and a home you will like.