Also, zoning and market trends matter a lot more than in residential, so it’s worth getting familiar with Tampa’s landscape.

and it's not only not cash, it's expensive money - for it to be worth using you'd need either (1) something short term, like a flip (not recommending that here) or (2) a very high return that beats the interest rate you're paying on it.

Quote from @Louis Hamilton: The property is worth around 800,000 and has no mortgage on it.

So if it takes 10,000 calls to get one closed deal  that's $4k per deal which would still be worth it.

The increasing barrier to entry results in fewer new STR's coming available for sale, but also fewer options for guests to rent. 

Also, for what it's worth, just because someone is in the military doesn't mean he isn't a bum.

I was chatting with some of my lending buddies at big banks and they are all backing away from the CRE space including office because operating costs are increasing more quickly than rents.

Consider defining clear roles, ownership percentages, and responsibilities upfront, and ensure you’re protected if the partnership doesn’t work out.Since you already own properties, it might be worth consulting a CPA who specializes in real estate for advice on tax strategies specific to your situation.

Given his spending habits during his first term, it might be a wash.Costs to build new properties will probably increase.

How much is the property worth?