Personally (as a STR-focused REALTOR), I would never give you numbers and tell you you can hit them. 

Hey @Mordechai Chaimovitz - It sounds like you are talking about Chicago's NW side because there are definitely tons of areas in Chicago where a 2 flat can cashflow well.I know for me buying on the nw side was critical to my personal well-being and life happiness. 

If you and another person own a piece of real estate as tenants in common then you both own real estate. 

I've done this personally and have helped a bunch of other investors do the same.

How we purchased our property: Combination of Savings, Personal Loan with interest from a family member (4% interest) and a cash loan from Wells at about 8%.

Each room has its own unique theme and personality, making the home truly one of a kind.

The key is to identify personal property from real property.

Did you have to jump through so many hoops and provide this level of personal information?

Do you have a personal connection to either of those cities/markets?

Signing the lease demonstrates they agree to the terms and then you can hold them accountable.If you don't do this, then the person named on the lease and paying the rent could disappear and you would have no legal authority to charge the remaining three for unpaid rent.