Are you sure the landlord collected May rent or maybe used one months free rent as an enticement to rent the property?

If the property does not have STR history and you do not have experience operating STRs, you can still get DSCR financing, however the rate will be higher and the LTV will be capped at 75%. 

I'd prefer free options. 

The recording can typically be executed within 2-4 weeks of closing with the title company, there is a typically a cost associated with the recording.Any similar experiences or cautionary tales regarding the use of an LLC for an investment property or STR acquisition?

Excel can easily do all this.You can likely download a free template that already has all the formulas you need.

Does anyone have any comments on working with Redfin end to end, as dual agent, buy then sell the property?  About to do my first flip and curious about Redfin, which appears to save a lot especially on the sell side ...

I have experience as an SFR investor (rentals), as a realtor as well as corporate experience in mortgage lending and servicing practices from a large bank - all of which I will leverage to grow my MLO career.

If I had a crystal ball I could tell you what the future holds with certainty…in my experience and opinion though, I believe you’ll find Lehi to be a great option for the criteria that you’re specifying.

Does anyone have experience in this market, or with this cost-segregation to write off income technique? 

Hey Tom I have a lot of experience here in Pinellas County, currently managing about 65 units.I would recommend staying out of Tarpon as they are strict 30 night minimum rental, and the demand is not as high as Clearwater/St Pete which also have 30 night minimums.