In Orlando, you have the opportunity to drive appreciation by buying a poorly performing, underdecorated STR at and drive appreciation by transforming it to a highly themed, well decorated property which books well.

I would think this is a bonus. 

The area is in transformation so I knew equity would happen over time as well.

You can get 1 sign up bonus a month and open 2 for each LLC.

However, with the bonus depreciation (maybe not the correct terminology) it appears to accelerate the depreciation and make the up front savings very significant. 

Starting next year, I’d like to use the property as a primary residence, but I’m trying to take advantage of bonus depreciation running it as STR for remainder of the year and take the paper loss against my spouse’s w2 income.

Once they've proven themselves, consider gradually increasing hours, offering incentives (i.e. bonuses) then lastly, increasing the hourly rate.** These are all rough #'s.

As a bonus, you can use it for your personal record keeping as well.

I am planning to perform a cost segregation study on the STR's I have purchased to take advantage of the bonus depreciation rules currently in effect to offset the tax consequences of leaving some $$ on the table coming out of my 1031 exchange.

The appreciation will be an added bonus and since you can not predict it and control it, do not account for it.