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.

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

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.

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. 

Now you just need to run this same play about 10 more times! 

As much as I want to say yes partnering up for steep local discounts is a safer play

You're on this website so you may think it will be REI, but maybe what you are truly a wizard at is playing financial marriage counselor for newlyweds, and then you will start getting all the newlywed business.

It's a nice benefit while you live there, but it shouldn't be the deciding factor in what you do next...it can play a part in the discussion, but the much greater benefit is your ability to sell tax free on your personal residence with a 121 exclusion.