The idea of settling at tourist places after retirement appear to be very fascinating. One of my friend bought a house at Shimla & maintained it for appox 10 years with a desire to settle there after retirement.
But did not settle there. The reason given by him are:
01. They could not could not connect with the house & people there.
02. Their children, relatives & friends found it too difficult to visit them because it always required lot of time, money & planning.
03. Travelling for them to meet their children, relatives & friends was also too difficult because this also required lot of time, money & planning. Because of this they started missing family functions , started feeling lonely & left out.
Decided to shift back to Pune, where their children stay & also started visiting for few months in year to their native place, where they could connect with place, people & friends. Visits to other places including hills are as tourist.
Hope it answers.