I can only speak for my own city, Greater Cincinnati.

Collaborating with local officials and aligning the project with community needs can streamline the process and increase support.Challenges: A significant challenge has been navigating zoning regulations and coordinating with local authorities to ensure the project aligns with city development guidelines.

Contact the City of Chicago on this.

That is the best advice I can give you.The forums have several folks that have gotten hosed by the city trying to do a STR even though they did everything right.

These examples occur in the same city or surrounding metros.

I have a great team that's very investor friendly Long Island, New York - just send me a PM if you would like an introduction.Anyway, it's awesome that you're here, and I hope you keep finding value on this platform.

On another G.R. house, I have used a program through the city "Get the Lead Out", a somewhat more popular program for some time here. 

Cities like Miami, Tampa, and Orlando offer diverse opportunities, from luxury properties to short-term rentals.While demand peaks during winter, when northern residents flock south, the state experiences fewer slowdowns in the real estate cycle.

I am interested in Rowlet, Rcokwall, FAte, Royse city area and my budget less than $350K.Thank youDan

All of these play into my bid as if it’s not 12 month seasoning and it’s owner occupied in New York my offer would be very different than if it was in Texas