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. 

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. 

Look more as a retirement play .

The other reason is that tax assessors may use different methodologies to value the property including revenue potential.The key items that play a role in the valuation of commercial real estate property include:Property Type: A storefront is for example taxed differently than an office building.Location: Rural regions tend to be taxed at a lower rate than urban regions.Government Spending: When there are different funding needs, it can determine how much of that revenue comes from taxes.Market Shift: When the market shifts, property values change which can lead to a change in the assessed value.Let’s talk a bit more in depth about how the commercial property values are determined.