(Remember the claims a certain former federal prosecutor and mayor of a major city would make outside of the courtroom…. only to not be able to make any such claims once in front of the judge?)

I have seen on my last trip to New York City formerly bankrupt hotels recover and make a ton of revenue off illegal immigrants.

City of Atlanta and Fulton County Tax dept work completely separate from each other.

Last year, my husband and I purchased an investment property in Salt Lake City that we turned into a short-term rental.

Learning from someone who is already doing it in your city would be the best next step.

You will need to get to know your property source, their team, their vendor partners and the city as a whole. 

Am I able to take the tree trimmings to another property that I have in the same city and put them on the street for pickup?

While in New York, I purchased a home (Airbnb) in the Saratoga Springs area, and my first multi-family property which was in Lubbock(2 Airbnbs).

It is a good sign that you are skeptical, so don't be frustrated.My advice at this point is to make a post on BP asking if there are investors or investor groups in the city you live in California that you can meet with in person who have invested in the cities you are interested in buying. 

And yes, the risk is that we're paying for the due diligence work up front, to potentially get denied in-front of the City Commissioners.What I will say is that entitling a 8-10 unit subdivision is the same amount of work and time as entitling a 50,100, 200+ unit subdivision, so it makes more sense to go larger.