This scenario played out with a lot of my family who moved to Florida and wanted to come back because of the fear of future weather disasters and other issues.

If they can't pay their deposit and the first months rent upfront their will be issues throughout their tenancy coming up with the rent.

Is there a way around this issue?

To add to the issue, Goldman Sachs bought up most of the Fannie May auction pools last quarter which added to a drop in inventory and increase in pricing for remaining, available assets. 

I don’t know the exemption clause you are referring to, and likely no one else here does either, but generally.......cities/towns have nothing to do with real estate licensing, that is a state real estate commission issue.

Seems like there would be more issues / risks to take into consideration and I wanted to get thoughts from those that have rented property with waterfront access.

I will state first see an attorney who is experienced in putting together entities.In the operating agreement is where you are going to want to put the accountablity issues front and center.

Looking at properties that are built in the late 1980's to help cut down on maintenance issues, I hope.

No issues, just the floor is pretty cold in winter.

The biggest issue you may run into would be if that the home he has already is an owner occupied home?