Figuring out
Rather than one big house, we have two smaller 3-bedroom, 2 bath cottages side by side and that's working out very well. The advantages of this strategy are:
1. We usually don't need that much space when we stay in SoWal, especially since we spend much of our time outside so we can stay in one cottage and rent out the other (this will also work at retirement time when we want to spend more time there). We also like smaller homes (there's a small home movement) because they tend to bring families/friends together, especially when they are well-designed with spaces for sitting and spending time together (as well as with well-designed spaces -- bedrooms -- for privacy). Big lazy porches are wonderful in small or large places because they become outdoor rooms.
2. We seem to get very nice young families staying at our cottages and tend to avoid big crowds of young people who like to party -- they seem to go to bigger houses.
3. Financially, smaller places worked for us. If we find out we're in a financial pickle someday, we can sell one cottage and keep the other.
4. We also like being high up on a dune because we feel more protected from storm surges. And we like having only one story because it's easier and less expensive to take care of one story places if you do some of the work yourself. One six foot ladder seems to be all we need inside and out most of the time.
All that said, someday we'll probably get our families together and rent one of those big rambling houses on the beach off season to get a first-hand experience at what it's like.
I don't expect to cover all of our cottage expenses with rentals -- it would be nice and we hope to someday, but right now I do extra work in my day job to cover expenses that aren't covered by rentals. With all the building going on, there's going to be a lot of competition for renters so good prices and great services will be critical. At some point, the area may have many more renters, especially if people from the north discover it, but that will be a while.
If someone purchased a home in SoWal a while ago, they could probably cover expenses though. We do cover mortgage, interest, and some of insurance, though, through rentals. But all those other bills add up -- e.g., utilities, association fees (our's are low but they still add up), buying stuff for cottages, maintenance, hurricane prep when necessary, etc. And it's work to take care of the cottages and guests (though it's work I enjoy very much).
Everybody makes their own trade-offs when it comes to buying/renting property and this kind of discussion helps people figure out what those trade-offs are. These were the things that we thought about and are happy about now that we've had these cottages a few years.