The numbers you see in population graphs of Chicago include the dying south side neighborhoods, it’s a completely different market. 

The quality of available tenant varies drastically depending on the neighborhood.

And still, neighborhoods can change, tenants can go rogue, things can break etc.I'm always looking for ways to help protect investors so I'm open to any ideas you have.

I love that these homes are in class A neighborhoods, I have seen this strategy work out for investors before but they were at least cashflow neutral. 

I have seen some properties on MLS that I contact my realtor and they may know right away the reason it isn't selling from showing it previously, or they can review the realtor comments that aren't viewable by the public on MLS.Other potential reasons I have seen properties listed on MLS for a long time. 1) Some investors may not be comfortable inheriting existing tenants.2) It may be it is a class C neighborhood. 3) Structural issues.

I really like the investment style you brought up, but c'mon Curt, if you're going to invest you should use your HELOC to buy the Yankees or Disney World! 

I work with a lot of MTR investors and what I am seeing frequently with multifamily acquisitions, particularly with new investors, is that they often test the property just like you're mentioning, as a way to dip their toes in the water and see what works in their area and for their personal style.

I think the A frame idea works great for this setting, but some have said the A frame style steeper peaked roof works better. https://www.instagram.com/redtail_cabins_adu/

Fix Flip- only do surface style changes- flooring, landscape, roof, windows, etc. 

From what we can find, houses with piers in the neighborhood have largely had to go very deep (90-120 ft), so estimates from local foundation contractors are ranging from 70-130k.