After retirement we traveled for four and a half years before we found what we wanted and became snowbirds
we did a combination of timeshares and rentals. Timeshares weren’t easy because we only owned two flex weeks but we did get a lot of extra vacations.
it was not easy moving every week from timeshare to timeshare.
we were avid golfers, we stayed two winters in Arizona, found the weather iffy and found it very difficult to get a good rate and a good teetime on golf courses. We had the more Luck in Orlando area, but didn’t like the area.
We settled in sw Florida, but most of the golf courses are private and owned by the subdivision. Subdivisions are like resorts with golf courses, pools, tennis, pickleball, bocce, private restaurants, and events. when we found a place we really liked we took the plunge. We have never regretted it.
as far as golf, we had guaranteed tee times in the leagues, and made lots of good friends
yes it is a hassle going back and forth. We only go once each way, so I have spent many holidays alone. There are pluses and minuses but the pluses outweigh the minuses. there can be problems at either home, but you hire someone to fix it.
I save enough on state income taxes to cover a lot of the second home costs. I do not have big homes, and I do not have high maintenance homes.
what hasn’t been mentioned is health, that is the biggest problem ith your plan. It will inevitably happen that you won’t be able to do it anymore. And you may have good friends where you live, but things happen and they will move on. Early in retirement I started a couples league in our northern golf community, thirty couples are now down to three or four.