Like Greg mentioned, I would be concerned with his/her responsiveness while I was living there. 

Great question and great responses!

With this strategy, who would be responsible for utilities? 

HI Jonathan, thanks for your response.

Drew I appreciate your well thought out response.

There was also a failing retaining wall in the rear of the property that completely blocked natural light form a handful of houses, and was technically on the property line and a shared responsibility.

Thank you for the response Sergey!

He's an adult, he needs to take responsibility.

Great post and many of the responses are valuable here. 

The numbers only look like they work because the calculation is only as accurate as the numbers we plug in. 954.00 for 12 months worth of maintenance on a duplexin Cleveland?