Is there an easy place to find a list of communities that prohibit either Short or long tern rentals on or around the island and or that answer frequently asked questions like mine and the others below?  

I have a good friend of mine who owns 2 acres of land  that is land locked.

Unsure of your price point, but Anna Maria Island is a great place to look. 

I know Hilton Head island very well as I grew up going there as a kid.

Living on an island, with a more limited fresh water ground source we are extremely conscience of not only well contamination but contamination into our surrounding marine environment.

Or as you have seen, that price range is landing you in less desireable areas. 

Here is the Uhaul data for 2021:https://www.uhaul.com/Articles...2021 U-HAUL GROWTH STATES1.TEXAS (2)2.FLORIDA (3)3.TENNESSEE (1)4.SOUTH CAROLINA (15)5.ARIZONA (5)6.INDIANA (12)7.COLORADO (6)8.MAINE (29)9.IDAHO (30)10.NEW MEXICO (39)11.SOUTH DAKOTA (25)12.VERMONT (26)13.WISCONSIN (13)14.OREGON (45)15.WASHINGTON (36)16.ALASKA (34)17.MINNESOTA (20)18.CONNECTICUT (43)19.NORTH CAROLINA (9)20.NEBRASKA (32)21.WYOMING (33)22.MONTANA (19)23.GEORGIA (10)24.OHIO (4)25.NEW HAMPSHIRE (23)26.WEST VIRGINIA (16)27.IOWA (24)28.UTAH (17)29.NEVADA (8)30.DELAWARE (27)31.VIRGINIA (28)32.RHODE ISLAND (35)33.NORTH DAKOTA (37)34.MARYLAND (46)35.WASHINGTON, D.C. (38)*36.NEW JERSEY (48)37.MISSISSIPPI (31)38.KENTUCKY (18)39.MISSOURI (7)40.KANSAS (21)41.ARKANSAS (11)42.MICHIGAN (40)43.LOUISIANA (44)44.OKLAHOMA (14)45.NEW YORK (42)46.ALABAMA (22)47.MASSACHUSETTS (47)48.PENNSYLVANIA (41)49.ILLINOIS (49)50.CALIFORNIA (50)2020 growth rankings in parentheses

Our “regular” cash flowing STR are in Smokey’s and Amelia Island, which substantially pay for our lifestyle.

In this barrier island community there is a difference from one side of the highway to the other.

Far southwest quiet side of Mount Desert Island (Tremont)2.