In the late 80's we started renting in Ocean Sands and we loved it, but the houses are tight together. Recently I've noticed vinyl siding replacing cedar shingles on many of the older homes which really changes the look of the area.
I have a few thoughts that might be helpful:
Buy a house you love, in an area you love
HOA's can be good for maintaining the look of a community, but they can also be a ****-show of narrow minded people on a power trip to enforce their will on others. they can also be expensive.
If you are buying in an HOA ask if they are involved in any past or current lawsuits
Buy the biggest lot you can afford, it will help with resale and possible expansion.
Buy the highest elevation in the neighborhood or avoid the low point of any street, people learn this the hard way when a storm floods their carport or lower level
Ask about prior insurance claims
If the house is 12-20+ years old make sure the HVAC units and roof have been replaced or that you have the budget for it.
Pool heaters are an endless expense, only do it for yourself
Find the top rental company in your area and find out if they will take your house into their rental program BEFORE you buy the house. ( My house is the smallest in my cul de sac but it brings the highest weekly rents because Twiddy is the tops and they have the best clients expecting and appreciating well appointed homes)
If you can find a house with well water buy it after checking the water quality (water bills in Corolla are very high)
Ask to see all the utility bills and review them ( this can tell you a lot about the current condition of a house )
Ask the sellers if you can stay in the house for two or three nights off season and pay them for it. You will learn a lot about the house.
Ask to see a copy of the property survey and check it to see it matches the current property, i.e. lot coverages, fence lines, encroachments etc. You don't need to start with a neighbor conflict because his fence is on your property or vice verse.
Drive by the house at all times of night and day to check noise, spotlights, smells etc.
Examine every house on google earth, make sure there isn't a water treatment plant, power station or something else hiding behind the trees in your back yard.
Ask seller if there have been conflicts in the neighborhood or are there any crazy people living next door.
Ask the seller if they are friends with any other homeowners in the area.
Find your own lawyer and find your own home inspector. Do not take a recommendation from your realtor. A home inspectors relationship with the realtor is more important to them than one homeowner they will never work with again.
Attend the home inspection with the home inspector, you will learn a lot about the house.
Vinyl siding is a very very bad idea at the beach, water gets pushed behind the siding and can rot the framing rather quickly.
Hire an HVAC guy to inspect the units, ductwork, drains etc.
Lastly, Only finance with a fixed rate 30 or 15 year loan always be conservative. Try to have a year's worth of mortgage payments in reserve. Don't count on rental income as the sole means of paying for the house.
Sorry this is a long response, but it's best to learn as much as possible as a buyer and it's also best to disclose as much as possible as a seller.
Lastly, keep asking your questions here on the board, I LEARNED so much from the amazing people on OBC regarding the rental vacation home biz. So many of the original crew here taught me so much when we bought our first house 14 years ago.