Hi kork--Just to build off of what Laura is saying, we did pretty much what she is advocating before we moved to the resort town permanently. We became friends with someone who had a condo in the town, and we were given a great deal to go down there and fill in his odd open dates. We did this for years. It got to the point where I'd call and say, "I noticed that you have two days open between your next two rentals. How much for me and my wife to go down there for those nights? He'd usually say something like, "Give me a $100." Anyway, we spent a lot of time down there, joined an Elks lodge, made some friends, etc. before we moved down for good. We absolutely knew for sure it was right for us. In contrast, we actually owned a second home in another beach town the whole time! Clearly, we didn't do our due diligence on our fit with that town. In short, listen to Laura. You could spend the next three years productively exploring different options that you think will work out for you and your family.