Stay with me.....Say I get a place that allows me to live rent free for the year I stay there or best case scenario put a few hundred bucks in my pocket and turn a Profit.

Consider Suburb areas around Madison and Milwaukee too. 

You've got at least a million bucks to develop this software?

For many years we have seen people move from Chicago to Milwaukee, very few the other way. 

Quote from @Chris Seveney: @Drew SygitSeeing a lot of posts here and on other forums about people buying real estate or making a quick buck, but that’s like someone bragging that they bought a stock that went up the first week.

Alternatively, (and I don't know Milwaukee):"Milwaukee is a great place to buy.  

Anyone who ever got a house trashed in a couple months for 15k damage knows what I mean.Covid did a number on many investors here in Milwaukee.

The real question is how many units are being built and what does net migration look like on top of demographics.I can answer the question for my market Milwaukee, because I have been tracking these metrics locally for the last 10 years or so.

You don’t want them denying a claim because you were trying to save a few bucks. 

Thats going to get you the most bang for the buck.