Trump has also done this, for example, he bought the Kluge vineyard/winery near Charlottesville, Va and put his son in charge of it.

Charging $500 per night in peak season is probably doable.The property management company will make or break you.

Either they include it in the mortgage, charge it up front or have other fees /higher interest to offset.

Specifically, how do you charge and what pricing is normal in your area?

I am trying to get an escrow anaylsis done once I get the exemption so that I am not over charged by Escrow as I am now.

If they suddenly found themselves with larger than expected/required/needed reserves they would then lower the monthly charges.

Prop Managers are notorious for over charging for everything. 

I got no problem throwing an extra $9,000 charge for that onto all of your turnovers.

If fix the pool, I cannot charge additional rent as I am already capped and I will be stuck with maintenance costs and I can't help but think that if someone drowns in a functioning pool and if it turns out that the landlord could have done "something" whatever that "something" is, he may be on the hook for a major lawsuit.

My first concern is the low monthly charge.