I admittedly have a bias against condos for the following reasons:1) HOAs - both a lack of control over fees and assessments, as well as potential regulation changes2) they don’t appreciate as much3) you have to work a lot harder to differentiate yourself from your neighbors. 

Co-ops have strict subletting rules that can change anytime, which could make things tricky.

•There are also different important rules as well as different regulations that you need to take note as well as you need to follow if you want to obtain this 1031 exchange.

This question is most likely best for a lawyer familiar with local regulations and code.

Rooming houses dwindled in numbers, and zoning regulations took out the rest.Now apartments in popular suburbs are as expensive as in center cities, and for people of even moderate means their own apartment or house may not be realistic financially.  

Strictly cash flow is missing the forest for the trees. 

As Sean Wagner mentioned, the city of Chicago has adopted their own regulations on charging what's commonly referred to as a "security deposit" you need to do it another way. 

Bottom line these are NOT federally regulated or state regulated loans.. they who have the gold make the rules.

Ramsha - most of the regulation for a STR is controlled by the neighborhood HOA.

I know there are some STR regulations, but it seems there are plenty of parts of town where it can be done.