Maybe adding a camper spot as well?

He strongly discouraged adding a backwater preventer bc he said he's seen it make things worse.

@Jennie Berger gave you the whole kit & caboodle on Chicago zoning so I don't have a ton to ad, however, I'd highly encourage you to engage an architect like @Samuel Pavlovcik or @Prashanth Mahakali, both are awesome local Chicago resources.

I'm in the Tampa Bay area and I will put an ad on Craigslist, Indeed or post in a group on Facebook for AirBNB/STRs. 

This added demand for rentals drives up rents.You must invest in a city with significant and sustained population growth to achieve rent growth that outpaces inflation.

Assuming property taxes + insurance added don't go above $1,100 total, you could maybe make this work. 

Unless you are buying at a significant discount, or are hacking it, or have some other value added strategy or plan.

total return from an RE investment includes value added, appreciation, tax benefits, equity pay down, and the cash flow. 

You can shift your perspective to enjoy what you're doing, yet reap the long term rewards by planting the seeds today. 

I added a clause in their lease that makes them responsible for weed and trash within ten feet of their space.