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

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.

Both Indy and Knoxville are major cities.  

I am researching the city and surrounding areas and seriously considering it for my first BRRRR.   

My niece moved from Redwood City to Seattle and was always complaining about the smoke and air quality, even though I don't think it was that bad  Ya I grew up in Silicon Valley and Redwood city is half way from San Jose to SF.