Know who are you targeting, what's nearby that will draw these people to your rental specifically.

I was thinking of it similarly, but without the specific calculations to go off, so that's really helpful.Your #'s are surprisingly accurate - $9k/yr principle paydown and with pool maintenance (I thought I should pay this too, so thank you for confirming), the cash flow isn't great. 

That way you will get other investors working in that area to give you more specific advise.

Revenue Ruling 2002-83 is the specific ruling that covers related party transactions. 

The more specific you can be about the problem you are trying to solve, the better response you will get.

Engage an architect, they will be able to advise you on how all of the issues written about here do or do not apply to your specific parcel. 

It'll be necessary to talk to professionals familiar with YOUR specific tax situation in order to address the pros and cons of using an S-Corp.

For Maryland and maybe more specifically Baltimore, search @Ned Carey posts. 

Can you be more specific with its location in Florida?

@Lindsey JohnsonLove to pick your brain on what worked and did not as I want to try this in a specific market.