Overall, zoning said, just put everyone on 1 lease as roommates and thats that, however NOT in writing, just over the phone. 

Option B is to find a co-signer on the loan that can help meet the income requirements.With this route, you probably have more options looking at single-family's with up to two roommates. 

Lived in it and redid the kitchen and other things and had a roommate that paid a good chunk of the mortgage and utilities.

Unless you want to have room mates it seems the best you can do is just reduce your monthly housing expense, but to cancel it out or make it very low seems very difficult. 

Which meant if I had four roommates and one decided not to pay, the other three were responsible for the rent.

When I rented the basement out, it was just a roommate of mine while I occupied the home.

You rent out the bedrooms to roommates (SFH) or live in one unit (2-4) and rent out the others.

I already rent a single family home in Sharpstown with 3 roommates, each paying a fairly affordable $380 a month in rent.

I also plan to find short-term housing, possibly with a roommate, somewhere until I'm comfortable jumping into the Chicago market.Areas I've investigated so far just via hearsay on here and other forums: Oak Park, Pilsen, Marshal, Mckinley Park, BridgeportAgain, I am completely new to the market so any advice is appreciated,Del

This also works with a home (ie you rent out the extra rooms to roommates).