Plus I hear NY State is going to be taxing short term rentals with a hotel tax. 

Virgin Hotel.

They are located in the Morrison Hotel building. 

If you rent to a couple with no kids and they have a baby, you are then required to delead the unit with the added expense of putting the tenants up in a hotel during the process.

The goal is to have a hotel spread across the region.

You could theoretically 3x or 4x your units under management by selling off each appreciated condo/apartment and transferring that money into multifamily units.Robert Kiyosaki called that strategy "trading 4 green houses for 1 red hotel" in Rich Dad/Poor Dad.

Also wondering if the expenses incurred during the trip (rental, hotel, etc.) can be a write-off toward this return as well or my 2020 return since the incidentals will actually occur in 2020.

With that being said if you are going to do a year round vacation rental there go on the low budget side under 85 a night and allow pets so you hold a competitive advantage to hotels.

Airbnb was invented out of the last recession so while there isn’t direct data for short-term SFRs, we do have data on hotel occupancy and RevPAR.

Living with friends, in hotel/Airbnb etc can be a red flag.