It really hit me probaly 10 years ago on vacation seeing wealthy people at the pool who can't see their own feet when they stand.

There's a pool on how long it will be until Morris Invest appears on the TV show American Greed.

Short term rentals in Tampa are saturated and unless you have a pool you'll have a low occupancy rate. 

:Class A Properties:Cashflow vs Appreciation: Typically, 3-5 years for positive cashflow, but you get highest relative rent & value appreciation.Vacancy Est: Historically 10%, 5% the more recent norm.Tenant Pool: Majority will have FICO scores of 680+, zero evictions in last 7 years.Class B Properties:Cashflow vs Appreciation: Typically, decent amount of relative rent & value appreciation.Vacancy Est: Historically 10%, 5% should be applied only if proper research done to support.Tenant Pool: Majority will have FICO scores of 620-680, some blemishes, but should have no evictions in last 5 yearsClass C Properties:Cashflow vs Appreciation: Typically, high cashflow and at the lower end of relative rent & value appreciation.

Drowning in pool.

It's been gutted to the studs inside, has a new roof, and has a pool (needs work plus a possible expansion), with room for new commercial buildings to replace the ones that were demolished or for an expansion of the motel with either more rooms or a few condos for short-term rental.I'm considering selling a single-family home that I own outright in another state (Lake Havasu City, AZ) to finance this deal. 

Who should handle what as far as the land and the pool? 

We are going to pool our money together and by the end of this year, we will have ~90k dollars to invest. 

For instance, if the top market rent properties have a pool, it would be important to have a pool.For 1-4 units, you could still get qualified for 75% LTV with 1.1 or even 1.0 DSCR.

Also, come resale time, the duplex would have a proven track record of producing income and has definable value, whereas a single family home is largely dependent on current market conditions and home buyer emotions and buyer pool at that given time