I'd like some advice on how to proceed at this point because it seems we've hit a road block.

Those houses caused me lots of pain both mentally and financially.

Less pain and less risk, especially if one has never done an LO before.Is the question sell for $11k cash now or deal with a tenant and funky agreement from a realtor lol for 3 years for $11k in the end?

I valued this comp over the comp 3 blocks south that didn't share the border with the utility field and was +$15,000 more.  

Other homes we own in the area:Richland Drive 1000 blockAlgiers Drive 5200 blockLochinvar Road 5300 blockKilarney Ave 1600 block So, I spend a lot of time in this area and our rental homes do very well! 

Legality: Chicago, like most big cities in the US, is going through legal growing pains with regards to Airbnb and the home-sharing economy.

Commercial loans are not restricted 5+ units ..Also bundling them may sound like a good option but if you ever have to sell one of them, it will be a huge pain

Studying is a pain.

And why is the CO is pain process?

One problem is getting enough properties on one block to make a difference.