It's a good idea to keep an eye on any rule changes and check resources like the City of Chicago's website or talk to a local lawyer who knows about short-term rentals.

Check out the Events tab at the top to find local and virtual meet ups.

@Joseph O'Sullivan start going to local meetups, talk to other new investors, but don't spend on trials because you will be looking without 20-20 vision if that makes sense.

You might find there was a local/state/federal grant that’s been used up.

Also, check out some of the local meetups that you can find in this forum!

In conducting a background check, I learn the applicant's current neighbors hate him, he's on a first name basis with the local police or he has a variety of other social/criminal issues chasing him.4.

Personally, I'd reach out to a local attorney or cpa that specializes in RE for guidance. 

An understanding of local rental rates may be gained via websites such as Craigslist, Rentometer, and Zillow.

Does your local board of health, building and zoning departments allow hair salon businesses to be run out of private homes? 

We live near Los Angeles County and are considering a local/out-of-state purchase.