I would think carefully about selling versus doing a cash out refinance.

Purchase price: $102,000 Cash invested: $6,000 Originally used as a short term rental, this property is now a mid-term rental (min. 30 days) and continues to cash flow.

This protects you if the lender/seller passes away or would try to sell the property out from under you and your seller finance agreement.

If you have an existing property that you've been renting out long term and want to switch it over to an STR to take advantage of this, is the IRS using the full calendar year to avg out the 7 day avg stay?

Almost negative on cash flow with all these repairs coming all the time.Next major thing I see is hvac in crawlspace and those ducts are loose and coming off.

Depending on the cause of the taxes it could be offset with write off's, deductions, carry overs, etc.You could always take out a loan through a cash out refinance to pay off or down the lien.

Not sure what I should do now to get her out of the property - this is in Florida.

I'm assuming I may have to pursue a cash for keys approach or potentially evict the one with the protective order. 

My goal is to have positive cash flow and do LTR.

That said, purely out of professional curiosity, may I ask what you're hoping to learn in the academy?