You don’t want small condos that are easily carbon-copy for example as you have no way to stand out from competition and it becomes a race to the bottom.

It is also my understanding that this would result in large tax returns (from depreciation offsetting my other active income) that I could use to continue to expand my portfolio. 

As you look to expand, you’ll find plenty of resources and advice here.

Then when Evolve takes it down, you will be able to shift to Hospitable easily.

You might also want to consider expanding your search criteria a bit.

I recommend finding a tax strategist who specializes in real estate taxation, financial planning and tax planning.You may want to consider working with your accountant remotely to expand your options.I would also recommend looking for a accountant willing to work with you throughout the year.

Congrats - do you ever think you'll expand a buy a true standalone STR of just happy with this current situation?

If you are looking to expand to other properties in the future, that option of a cash-out refinance or HELOC on your appreciating asset is always there. 

Could you expand more on what other things are important to you in this investment? 

It will easily be your most trusted resource with your specific case.2) Fema will not cover anything business-related I was told multiple times.