Commercial Due Diligence...what am I missing?

[Ryan Slicer]

BP community,

Background:

A few things to note before I get into this thing. I have been quiet on the forums, but have listened to most podcast episodes, I belong to meetups etc...I live in an up-and-coming, somewhat urban, Cincinnati neighborhood of about 30,000 residence. We have made some solid connections here and have invested in this area only as our vision is to have a positive impact on the community here through real estate. On this journey, my wife has become a real estate agent and has focused her attention on the area as well.

Situation:

A few months ago, I cold-called the local head of city council because I found out he owned a commercial building nearby (which piqued my interest) and we met for a beer, chatted about the possibilities and then things went radio silent. Earlier this week, he texted me asking if I was still interested and we met at the property to walk through. We got to talking and because of his insight on city council, he knows of several other developments slated for the next year or so which will ideally take our town from "up-and-coming" to "the cool part of town". Why does he want to sell?? He now has 5 kids, a full time job and other investments. He seems to care more about who the property goes to, ensuring that the buyer has the same aspirations for the development of the town, as opposed to price. 

My plan is to buy & hold, fix it up because it's a wreck and rent to tenants who want to have the best interest of our town in mind.  

Question: 

This has been long-winded, I know. But I felt it important to lay ALL of this out because its a little cumbersome. 

My question for you all is:

What questions should I be asking at this point? We have only walked the property once and texted a couple times. He knows I am interested but that's all. 

What are some good resources when it comes to due diligence in this area? I don't want to buy it and get burned with something I have never heard of.  

What am I missing? 

Thanks for any feedback!