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

This could give you the cash you need for the purchase and also eliminate your personal guarantee for the loans.

Then, each person with money in the deal would get an 8% preferred dividend until they get all of their money back.

You might be able to get around the fact your entity owns the property by either transferring the property back into your personal name or by some personal guarantee or cross-collaterization agreement.

If you've never done it and never looked at properties anywhere in person, how will you know what any of the numbers even mean? 

I’m not convinced it makes a real difference unless a person has a unique setting.

Figure out which method makes the most sense for you and look at the numbers for at least 10 deals.

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. 

However, I think for the average person this is probably not true. 

@David To In Texas there is a way of using tenant personal property to pay past rent.