So I am going to hold off for now and focus on an SFR. https://www.loopnet.com/Listing/9335-S-South-Chicago-Ave-Chicago-IL/16404915/https://www.loopnet.com/Listing/7421-S-Coles-Ave-Chicago-IL/17239821/But these are attractive numbers, I would like to know what the challenges are going to be and if such an MF in that region can be managed 100% remotely through a property manager.

Zillow, et al. is, so far as I can see;  using real estate listings as a way of attracting web page viewers to view the advertisements which are also on the webpage.  

If there was ADU specific financing, that might be attractive (none that I'm aware of?).

There is a sequence you need to follow, you attract attention every day of the week leading up to the open house.

They are attracted to a nice older home near downtown.

I replied to his most recent email that maybe I need to update the bathrooms a bit to be more attractive and asked for contractor references.

I don't know if the profession attracts them, or if it just encourages them to become that way.Hopefully what you had was a lack of communication with this guy, but maybe not. 

Generally west Germantown is looking more attractive, but even within that there is huge variation.

It is on 33 acres and has a lot of features that make it attractive for assisted living including views of the Mississippi river valley, 33 acres of land with walking path, indoor pool, beautiful flower beds and landscaping.  

Trust me, they won't call peco because they owe peco thousands.the new inspectors would make a non hands on landlord broke for sure,but again, if you know ways around things,your okay.You have to be like your tenants and know how to work the system and forget about you morals from time to time just like your tenants.Landlords are attracted to Pottstown because of cheap properties, but cheap isn't always good.