@Cameron KlineHow do you know he has been successful Would a successful person put no money in a deal?

I did not personally value the deal all that well because this was before I got seriously involved in researching real estate.What was the outcome?

For cash flow vs appreciation, that is a personal decision. 

Each person has their own skillset they bring to the table. 

While we are actively working on our personal trust...

I am personally strongly against any type of mentorship program or course.

Require at least 5 real references and call them yourself and require 3 family/personal references. 4.

I, personally, focus on midwest markets, specifically Detroit and Memphis with 7 doors across those cities.

My suggestion would be to come out to as many in person meets as possible (https://www.biggerpockets.com/forums/521/topics/1177645-tax-...), ask tons of questions, and figure out how to hang out with people who are doing what you want to do (add value, work for free, do anything to get that experience.What area of Chicago are you looking to invest in?

It all comes down to where you balance your personal perception of risks to the potential reward.But, in hindsight, I sort of align with Melanie.