IF the City does not limit to four total, there is a scenario where the City MAY allow up to 10 total units on single family zoned parcel

She will probably game the system for the next 6-12 months, but that's what you get buying a property with a non-paying tenant in place, in an anti-landlord city. 

Michigan and any other reasonable Midwest city.

And I don’t mean something like saying you want to invest in New York City, I mean an expert on specific neighborhoods you have chosen for a specific reason.

Tenants in many markets already believe they pay too much (contrary to recent studies that show rent to property values have never been lower for the large US cities).If my insurance costs are not double my current rates over the next couple years, I will be pleasantly surprised.  

From what I've heard, CA is very ADU friendly so check with your city on what's allowed.

do you have issues with the city if there are cars parked on the street or lawn?

One would be amazed at how many cities were platted between 1900 and 1940 in CA then the slow build out started..

Chicago cap rates are actually much higher then other comparable sized cities.

The city offers more affordability compared to the DMV area, with many renovated homes selling below 350k giving you a better chance at finding a property that fits your budget while avoiding sky-high prices.