For Milwaukee the answer is no.

But by the end of the hard sales pitch at least 2/3 of the people stand in line to shell out big bucks for a week end boot camp to hear what the so called gurus have to say.

Milwaukee and Chicago have very similar housing stock. 

I was able to get in at a lower cost basis, and the property didn't cash flow while I was living there (this is a common misconception with house hacking) but I lived almost for free - Only had to kick in a few hundred bucks a month. 

Now I am 15 years into this and some of the properties I have not seen in years even though they are all here in Milwaukee (we do annual inspections though).

If you are charging full 20 bucks it would give me pause.

I know in tennesse there are 300k houses paying like 600 bucks a year in property taxes.  

I always expect about $6,000 for one of our SF in the Milwaukee suburbs, but that is different from an apartment.

If your looking for the least amount of risk and biggest bang for your buck I would look for a company that is a reputable turnkey provider thats actually in Detroit and offers things such as an efficient boots on the ground team, all sorts of established local relationships, solid in-house management, an operation that is highly skilled and well versed in section 8, a company that has proven relationships with both out of state and local lenders.

We have a chronic housing shortage in Milwaukee, both for rent and for sale.