I personally like the strategy of "kicking it down the road" over and over until you die. 

It keeps me on schedule with reviews of their payment history, lease compliance, in-person property inspections, rent increases, lease term updates, and more.With even a modest 3% increase per year, their rent would be $3,054 in the third year, almost $80 a month more than you currently propose.

Based on personal Experience from BP Members...Any feed back will be highly appreciated..  

@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.

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?