My two cents-rent first. You will never really have a true idea about reality here until you actually live here. You could spend 10 weekends here and never really see what the big picture is regarding all the different areas. We rented before we bought and that was a good move on our part. We figured out QUICKLY that we wanted no part of full time residence in a neighborhood where short term rental houses built to house ten to twenty people predominate. We also figured out that another seemingly Grayt neighborhood sits low and is so fantastically over populated by biting flies in the spring and mosquitoes in the summer (not to mention high tourist volume in the season) that there really is no chance at living outdoors without slathering on repellant (and that does not discourage yellow flies). You owe it to yourself and family to LIVE here and take note of how dense certain neighborhoods are in the busy season, how bad traffic might be in certain areas, whether a nearby restaurant will fill your house with the scent of deep fried whatever all year...there is no need to jump into the market without really learning about it first. Prices are not going to skyrocket like they did before, and even if you do miss 'the bottom' and shell out an extra $10K on a house, that is money well spent if you will actually enjoy living full time in said house. Trust me on this.
Thank you so much for this info. We have definitely decided to rent first to scope out the neighborhoods and/or lots to build. You made some good points we hadn't thought of yet (low lying houses, restaurants..etc). Priority is living in an area (when we buy) that does not have rentals...you hit the nail there.
We have been lucky to friend some folks that are currently full-timers and have given some great advice to us as well. We are full speed ahead with a Jan arrival date. 30A get ready.