I'm very interested in multi family and possibly hotels that need rehab so I can add value.

Being a tourist destination hotel taxes are a huge source of income for the city but at the same time it does not seem as though the city is completely against the idea either.

I'm asking about people that construct or purchase large apartment complexes, condominiums, commercial buildings, hotels, etc.How do they make them cash flow in an amount that is worth all the trouble it takes to build and manage them?

Especially since the airlines / hotels are known to devalue their awards charts. 

It's supposed to end up being similar to U Village. a new high rise hotel is going in, in the same neighborhood, 25+ stories I believe (Hilton?

To be most profitable, know that you shouldn't stay at your property during those times.The easiest route for you would to buy a Condo-Hotel.

My future is real estate flipping houses to pay for rentals multifamily is the path I want to take (4 green houses trade in for 1 red hotel).

Tiny homes and airstream communities/ hotels seem to be the hot thing now!

They will give you a 90 free trial and use Hotel/Airplane pricing model that factors in local events, avg. rate of hotels, avg. rate for other Airbnb listings and their occupancy rate to change your room pricing every night.  

Their future home is not going to be available until then, they would be sleeping in a hotel, so the closing time frame was incredibly important to them.