Without an influx in new construction we are probably going to stay on this path, because outside of 600k new construction in the suburbs, we only have what we have in terms of houses.Wisconsin is generally a landlord-friendly state, but Dane County (Madison) keeps getting more and more landlord-unfriendly, Milwaukee is definitively better in that regard.

Oh and listen to @Dave Foster, he knows a lot and was my go-to guy for the 1031 exchange we did! 

How can I help you achieve your goals in exchange for you helping me?)

If so,Have you considered renting and turning your current unit into a rental investment (enabling a 1031 exchange after 2 years of rental income) ?

I thought the whole exchange was odd since I told him from the beginning I wasn't even looking for funding at this time but he definitely wasn't legitimate. 

The process you are referring to is what we call a consolidation exchange, where you would sell multiple properties to buy a  larger property.

In exchange, the former homeowner lives in the home until their death rent-free.

I'm thinking about doing (my first) 1031 exchange into a 4-6 unit property.

However, there were also multiple instances when one or both of us felt dismissed or disrespected during our written and verbal exchanges with Ryan.

Mentee's have to realize that there needs to be a true value exchange.