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.

But, moving forward, while I'm still contemplating property in Florida, I'm thinking out-of-state investing (Georgia and the Carolinas, in particular) will be a better play for my investing goals.

I've heard a lot of old timers also say they've never seen anyone play the market and have long term success. 

This is a tough question to answer because there are many variables that come into play.

If your plans depend on selling this new, smaller rental for a profit that's a big risk.Now, if you can buy something that needs work, do the work and force some appreciation... that's a much smarter play.