The US Chamber of Commerce Foundation put together a little pamphlet looking at municipal business regulations in 10 major American cities. They combine all the information into a somewhat arbitrary aggregate index, but some of the specific findings are striking. For example, if you want to start a professional services business in Chicago you are basically facing a dystopian nightmare:
Chicago also makes this relatively expensive with $900 in permitting fees, but New York charges even more — $1,306.
Things like the efficiency of the business permitting process is not, in my experience, typically a big issue in mayoral elections. But it can make a fairly big difference to individual people's lives. Immigrants, for example, often find it especially burdensome to navigate a complicated permitting process because they don't have as many language skills or local contacts as native born Americans. Chicago is responding to this with special programs to help immigrants deal with the system, but simplifying the system might be smarter.