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

I have personally been the guy who hasn't pulled permits and got caught...by far one of the worst experiences of my investing career.

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.

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

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

Also, you don’t need a business license just to look at properties, but if you buy a bigger property, like a multi-family unit, you might need a certificate of occupancy, depending on the local rules.For business trips, most expenses can be deductible, but if it’s part personal and part business, you can only deduct the business portion.

Do you have a 501c3 that you operate under (and rent the house from yourself), or do you purchase homes with an LLC or personal name, and run as a regular business? 

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. 

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

In your experience what are some ways I can understand the intent of the person who said they're interested in buying?