For my wife and I it has been family which has been the deciding factor in our present residence. I have property in the area of Shelton, WA on the Hood Canal - 2 acres. I have kept it for many years thinking it would be where I retired. In my youth I lived in FL, TN, WA & OR, then went to college in CA, then in TX. Lived after college in AZ, TN, NC, WA, MI, and now KY.
I still have the WA property, but frankly when I visited the area the last two times I left feeling it is a zoo. You can't fish the areas I used to fish, the traffic is horrible, building costs are ridiculous, codes and permits insane, and what used to be a warm and friendly community is no longer.
We have the means to travel when we want, but it has been family and friends which have been the deciding factor for us in staying in KY. In the future we may consider moving further south, but I really don't like FL or TX in the summer.
We have discussed renting in FL a couple of months during the winter. This year we went to Florida for a week. But, honestly by the end of the week I was looking forward to going home.. Every year in the fall we take a few weeks and travel after school is back in session. For the present it seems to fill any desire we have to relocate.