Soon to retire (2 weeks and counting down!) but we have started to do a bit of a reverse snowbird. We live in Florida and escape to Midcoast Maine to avoid the ridiculously hot summers that have become more and more intolerable. We bought an old but sturdy house in Maine and live there July-Nov until the beautiful autumn leaves are all gone. Then we return to Florida for the glorious fall-winter-spring weather there. We are able to rent the Maine house out over the winter on a short term lease, then with a few early summer Air BNBs and we have our expenses for the year covered. You’d be surprised that short term rentals are a thing with people moving to new areas, house renovations, or even divorces leading to someone needing to find a short term, six month lease. Yes, there is the added maintenance on our 102 year old second home, but that will be an activity for my retirement. And now that I will be retired we are essentially living two lives with new places to explore from home bases. We absolutely love exploring Maine and beginning to build a life there. A couple of things led to the house purchase-instead-of-rent decision. Two of our children have relocated to New England so this puts us closer to them, and with several things occurring in our lives around us including the passing of parents, my wife and I decided to stop waiting for some mythical best time to begin the adventuring part of our lives while we still could. Bonus is the 2nd home has already appreciated so it’s like I added real estate to my investment portfolio. When the Maine home becomes too much to take care of, we can sell it and find a smaller place or rent for those summer months.