Maybe adding a camper spot as well?

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.

They exist but are far and few between.After bumping the rate to 7.5%, adding 5% to Maintenance, and increasing taxes to $2500, I would need to increase rent to $950 to cash flow.

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

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

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.

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

I sent you an email so I could be added to your group!