I plan on calling financial plus credit union, Elga credit union, Michigan State credit union (they have some unique car loan options so might be flexible), and finding others to get a portfolio loan.

It is a very unique property due to the fact it sits on an acre lot with an old 30 x 30 barn built in 1950.

If you could A) continue to provide him with a vision of what a successful endgame can look like (because each individual's successful situation is unique) and B) cultivate ownership of his REI future while C) providing tools to get there at a good pace for his development, that would be an enviable setup for many at the tender age of 14.  

It's a unique situation in that the average Chicago house hacker has great credit and strong income but likes to put as little as possible down.

You need a sharp object.

@Derek Dombeck very unique ideas.

I have a unique Multi-family real estate idea.

@Bjorik Mutize the overall objective is leaving the rat race through real estate.

Chicago’s neighborhoods are unique, invariably different, and constantly changing.

I am an investor myself, so I have a unique perspective about structuring, terms, and especially looking ahead at properties #2,3,4 to set you up for future success.