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.

If you go that route, make sure to adjust your holding costs as it will likely take you longer to do those tasks than a contractor.

@Derek Dombeck very unique ideas.

I have a unique Multi-family real estate idea.

(Style of building does matter though; side-by-side units tend to have less turnover and drama than buildings with 2 units up and 2 down.)If my assumptions about the area are true, we'd be at $300 for management - a $75/unit minimum - effectively doubling your PM costs over the average. 10% of $1600 for 4 units may not even cover our costs in some months - send someone to post a pay-or-quit notice; another for a maintenance inspection; then add typical common area management, collection and accounting tasks ... time is money. 

If you have someone that will get the leads for low cost per lead then save your time for more important tasks.  

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.

@Shronda Sledge Is this property in a rural area that is making it tough to comp or a unique structure to the market?