I bought a cottage in SoWal and LOVE it. We made some of our best memories there, so much so that my daughter wanted to have her senior high school photos taken at the beach across the street. Here are a few things I've learned:
1. I have no regrets, only great memories with family and friends (and some SoWal friends that sadly, I haven't seen much but will see again in the future when I'm there more often. If you're going to make great memories there and you have the money to pay for it and won't depend on rental income to pay the mortage and you have other investments and savings/retirement, you'll be able to enjoy the memories you're making with great peace of mind.
2. I like renting it out and using a management company to take care of everything because I work full time and can't get there often right now (but will in about 3 years... countdown has started....). I actually have two cottages and I go "in the hole" about $10,000 on one cottage and $20,000 on the other cottage each year. That's a lot of money since 2003 that could have been invested somewhere else, but I probably would have put it into the stock market and lost some of it anyway, so I'm feeling pretty good (the cottages are just part of my investment portfolio and they make me very happy). So far, I can cover the $30,000/year; if I can't in the future (e.g., kids in college), I'll sell one cottage (and I'm glad I bought right before the prices all went up and crashed, so I'd be OK, but that didn't work out for everyone which is why you heard so many warnings - everyone here knows people who got burned and are just trying to make sure that doesn't happen again).
3. I don't worry too much about what happens to the stuff when it's rented. The gain from the renters (in good will, having people in the place when I'm not there, stuff they've kindly left behind for others to use) has far outweighed any losses (very little has been taken or broken). I don't put my best stuff in there, but I do have some sentimental things in there (old furniture) and I'm not worried about it. If it's meant to break, it will break.
4. Personally, I like having small places (two side-by-side 3 bedrooms but in 1100 square feet each - brilliant use of small space) because it's less likely that I'll get large groups of people -- e.g., unsupervised students. I advertise my places as family-friendly, which they are and with nothing to do in the area except sit on the porch, pool, beach. Doesn't sound too appealing to partiers and people looking for action (which is good). Also, with the two side-by-side smaller places, when I travel (or guests travel) with larger groups, they can get together when they want and also go to their own cottage for privacy. And I can go down there and stay in one and have renters in the other. And if I decide to sell one, I still have the other.
5. Don't expect the management company to get all your renters (or even most of them). Use VRBO. And the rental company will never clean/maintain your place as you would, so expect to go there and have to follow-up on cleaning/maintenance. Sometimes I go there and the places are in great shape. Other times less so. But I have a very good relationship with our management company and I'm glad they're there.
6. If you're concerned about hurricanes, find a place that's up on one of the high dune areas of the SoWal area. Won't help with wind and rain, but sure can help with storm surge. Also helps to get a place that has passed the most recent storm codes (e.g, roof, windows). Get on SoWal.com during a storm/hurricane and you'll get up-to-the-minute news on what's happening. Don't worry about the beaches looking pretty torn apart after a hurricane. It's interesting to watch the beaches change over time. They were absolutely stunning this past August with fluffy white sand and I must say they were stunning after Hurricane Ivan. It really was something to see what hurricanes can do and how Mother Nature Works. I'm a wiser person about the beach/nature now than I was when I first came here in 2003. If you're on a dune, the stairs to the beach will get washed away every now and then, but then you can go to the beach in some of the flatter areas and the association (if you have one) will charge you to build new stairs.
7. If you buy a place with an association, remember that association fees go up. Our community has VERY low association fees because it is small and the landscaping is natural (no grass or fountains to pay for).
8. Remember maintenance costs go up over time (though furniture/set up costs go down). Now that the cottages are 6 years old, I've had to do power washing, some painting, and other things like that. I could have let it go, but I like to take care of them (and the neighbors/association like us to take care of our places).
9. If you can rent your place in May - August, that's the peak season and you'll make your $ then. You then have the rest of the year to visit unless you get snow birds (we have snow birds in both cottages for some of the winter, at least until I become a snow bird myself). Snowbirds rent for a song in the winter, so you don't make much at all but it's nice to have someone in there and it's nice to know the places are appreciated by happy snowbirds who got a great deal. and having snowbirds in the winter brings the area some business during the low season.
10. Beach front is certainly nice if you can afford it. You also have to consider the costs/hurricane risks. Having a view is great, but many people bought thinking they'd have a good view and someone built something in front of them. So be careful if you go for the view and check out the risk of losing it. Consider what kind of constructions/changes could be happening near you as well. We don't have a view of the ocean right out our windows - we look at the native plants and trees which is also very nice (and some native creatures as well). A view would be great, but can't say once we made the decision not to have one that I've yearned for one. I just walk to the beach and enjoy all the view I want.
11. It's nice to be a very short walk to the beach, short enough that you can carry a lightweight Publix Beach Chair back and forth in the heat and not get cranky.
12. Talk to people about the advantages/disadvantages of the different communities along 30A so you can find the right fit for you.
I LOVE our cottages and everything SoWal has to offer, especially the people (friends I've made), the beach, and the FOOD (lots of amazing food). It has been fun getting to know SoWal more intimately - 6 years and I still have so much more to see and learn. No regrets, only great memories and great expectations for all our future visits there.
Enjoy the dreaming and buying of a place of your own and just pm me if you want to know any of the other things I considered when buy the cottages or if you have specific questions. It's good to hear the warnings as well as the good things so that you can make the best decision possible for the long-term. I'm a bit of a worrier so I thought through many of the details before buying (e.g., be on a dune in case a hurricane hits, go for low association fees if possible, spread the risk between two cottages in case I had to sell one, buy a smaller place in case my income changes, etc.). And now all I do is think of the good stuff with the cottages and worry about nothing when I'm there. It's truly a haven and great for the soul.