Here's my take on the decision:First, let’s look at the pros and cons of paying off your current short-term rental (STR):Paying Off Your STRPros:-You Eliminates your largest fixed expense (the mortgage), which increases your cash flow significantly.

And also being next to a base Im thinking about short term renting, or Air BNB How did you finance this deal?

Long term play would be to either use it as a short term rental or 1031 exchange it after 2+ years.

Long story short, all this means a net negative cashflow. 

Especially if using the funds short term, there's not too much interest.

Be mindful of short-term capital gains tax, as profits from flips held for less than a year are taxed as ordinary income, and frequent flipping may result in self-employment taxes.While profits from flips do not qualify for 1031 exchanges (since flips are considered inventory, not investment properties), you can minimize your tax burden by deducting allowable expenses like renovation costs, loan interest, and holding expenses.If you're considering diversifying into rentals, explore opportunities to benefit from long-term tax advantages such as depreciation and lower long-term capital gains rates.

The quick short answer in my opinion is this: If you want growth stick to the small multis that you know and once the mortgages are paid off retire fully.

Short of selling my entire portfolio, the liquid capital for the down-payment remains unattainable. 

Short term rentals in St Pete are technically illegal but it doesn’t stop hundreds of other investors from doing it.

I reached out to Ward Hanigan but that short course does not look available currently.