The federal tax code establishes stringent criteria, including guest stays limited to seven days on average and the provision of basic hotel-like services, to qualify for this advantageous tax treatment.Understanding the mechanics of the short-term rental tax loophole is imperative.

The train is going to stop at one single station and then you'll have to go to your hotel or Airbnb.

Many of the "everyday" expenses that most people have I don't count since I am always travelling and at a hotel during the weekday.I have been thinking of going back to doing Uber Eats or Doordash. 

I asked the insurance company what happens to him if it’s unlivable and they said they will reimburse me for missed rent, but if he is displaced it’s on his renters insurance policy to pay for hotel or whatever he decides.

A hotel you always have to show an ID.Other thing is insurance.

I'm far from an insider on local politics, but my impression is that the hotel industry has a heavy hand in city planning, which IMO stifles some of the intiatives that would potentially preserve our quality of life despite the rapid growth.  

Is there any tax advantages of building a multi family, hotel and keep it for the cash flow vs selling it after occupancy?

I think the most that I need to wait is 2 to 3 weeks because the client is living in the hotel right now. 

P.S. the cash flow from this investment will cover the cost of an Airbnb or hotel room when you visit.

Running a STR is like running a mini hotel, you are more in the hospitality biz.