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

Continue to scale my personal RE investments and learn!

There's a common belief that your tax person should also be an investor themselves.

You’re going to be personally sued no matter the cause of the loss.

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. 

@Reyna AyalaI personally feel this is overkill.

You'll never get the confidence to invest from another person or guru.

No problem, I had cash from a refi, a HELOC, and a personal LOC.

I would be happy to discuss structure and feasibility as well as insight into my personal finances/personal stake into a deal with serious lenders/prospects.Even if you are reading this post and are not a lender but have valuable insight or experience with flips in Charlotte's market, please don't hesitate reaching out.

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