For a Mid-term rental, I would say furnishing it with the cheapest but most durable furniture possible because of the frequent turnover.

Not a fan of loan guarantor fees in general.Sponsors track record in these types deals across multiple economic cycles (when I see these types of deals, I mean acquiring new construction multifamily in the area)I am sure if I saw the deck, I would have at least a dozen more questions.  

Some counties will only give you a list by email or tell you to look at the county legal newspaper, but many counties post a list on their websites, which are updated frequently. 

Buying a piece of heavy equipment like an excavator or Bobcat can definitely save you money long-term if you're going to continue to use it frequently.

One where a kid stuck a stick into the A/C unit fan which over heated the 20+ year old pump.

If you plan to make frequent and extended use of the money, the a cashout refi probably makes the most sense.

Initially I was worried about having older guests more frequently which is what I have heard about VRBO.

Most buyers and sellers are vulnerable because they don't buy/sell real estate frequently; licensed agents (me) take pride in "guiding and protecting" clients from transactions that can go wrong. 

The problem I see is passive investors frequently don’t invest on a risk-adjusted basis.  

I would avoid Holly Hill, Daytona's ghetto, like the plague because the oldest profession seems to be a major profession there if you know what I mean.The Daytona area is a bit or of my way, and my brother-in-law had frequently complained about finding a nice property that turns out to be in Holly Hill.Nearby Ormond Beach and Port Orange seem like nice communities in comparison.