Also, a nicer home will attract nicer tenants.

In the US, the cost of land, labour development fees and even tax abatements are very attractive.

The clientele that you might attract with a 'medium term rental' would be people who are looking for a place to stay for ~1-6 months.

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?).

lolOffer is still on the table to send you some free BitCoin if you sign up for a wallet to send to..

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.