I live on Long Island, so investing out of state would be easier point of entry in terms of cost 

I don’t have any experience doing this personally, but I’m on Long Island and this is exactly what the couple who owns the property that my girl lives in does.They bought a home, lived in the home while they renovated it, added a basement unit and rented it out.

For example, Isle Royale NP is an island in Lake Superior with only camping.

My thought ahead of time was similar to you “I want to try these” - thinking I could self install islands of carpet in bedrooms myself and have the ability to patch if needed between tenants.

The first floor features a renovated kitchen with a large island, connecting a cozy sitting room, a living room with a 55" TV, a dining area, and a spacious back porch.

The first floor of this private home offers a bright renovated kitchen with a large island centrally located between a cozy sitting room, the living room with 55" TV, a dining area, and the spacious back porch.

On Hawaiian island, the number of visitors to Hawaii from the mainland US decreased by 10% but specific islands like Maui got hit the worst by 30-40% (?).

I know a European fellow who bought an island and Airbnb the entire place. 

SupplyLas Vegas is unique because it is a tiny island of privately owned land in an ocean of federal land.

If it's a County island, there is an understanding between the Cities and the County that they will work hand in hand.