In my experience the Landlord / Tenant laws are less favorable in Chicago and I have concerns in how the budget deficit in Illinois is going to play out.

This is where the operating agreement component comes into play.

There are countless factors in play here and it makes answering this question or assessing cost very difficult.  

Even with a fence, I wonder if one could argue the bridge isn't an "attractive nuisance" because what child wouldn't want to play on that bridge even if they needed to climb a fence to do it. https://www.law.cornell.edu/wex/attractive_nuisance_doctrineSo, I would either remove the bridge while its a rental or add the the railings.

Decide which game you want to play.

The Tampa Bay market is more of an appreciation play than a cash flow, so I don't really know your ultimate goals with this rental.By the way, I saw that you are here in Sarasota.

If it is to play it safe and have a feel for the type of actual operating income that the property can produce before you put debt on it, that's a safe and solid idea.The good news, however, is that you're likely going to be purchasing a furnished property.

I like to use a spreadsheet to make it easy to play with the numbers.

Meaning, DTI, and taxable income are in play and can limit your HELOC amount also impacting the amount to qualify for and or making it extremely difficult to qualify for anything at all.- Vacancy rate factor and bottom line Schedule E income will be used to calculate the rental, no the gross DSCR lease amount.

Decide which game you want to play.