I'm looking to buy my first rental property this year or next in Florida and I recently attended a workshop on how to save on taxes using short term rental properties by a tax strategist named Karlton Dennis.

If there are 8 months left, not much you can do in the short term.An investor can buy the deal, and wait until the lease expires, and send a non renew.You can always offer one of the residents an incentive to leave, such as cash so you can have a vacant unitGino

This is assuming you are talking about a short term rental and not sub-leasing as a LTR.

Deciding to BRRR (Buy, Rehab, Rent, Refinance, Repeat) instead of selling makes sense if the cash flow and ROI are better with the property as a short-term rental (STR).

I think this is the gift and the curse of a still emerging asset class (short term rentals) - as it becomes more "institutional" i.e. more like commercial real estate with more sophisticated buyers then financials and systems for this will likely become more streamlined and stable, but we are still in a place where the buyer pools are more newish investors or typically residential basic investors, so not has experienced or sophisticated evaluating investments based on a detailed financial analysis like more seasoned commercial investors likely would.anyways, just a guess on what might be going on here

I don't want to fork over 50 K into a tree that will rot in a relatively short period of time.  

Your going to need to show proof of rent payments and/or short term rental income.If your buying a primary 2nd home and intending to use it as an investment property I would strongly refrain from that activity; especially if your posting about it in a public forum ;).Best of luck.

Ahead of schedule on inventory, short term pain for long term gain.

Stick to short term goals. 

Is there a community you are aware of that I could find a private lender that would be interested in terms like this and could provide the cash out refi shortly after rehab is complete with a competitive rate?