I live in Chicago, and I'm looking at various metro areas within the midwest to potentially plant some roots and start developing relationships (with PMs, Agents, Contractors, etc.)My question is, what are the different variables I should look at when choosing the optimal location?

You have to get at the root cause of his objection and fix that.

@Adam ChristopherI considered this, but is it really as tricky as they are saying with the roots, water line and needing to go out horizontally 8 ft in order to get sone working space?

Landlords helping other landlords to become better landlords is a good thing, but the rogue landlords need to be rooted out!

Rooting for you.  

I would even so bold as to say the OP stands a better chance of finding a Canadian attorney and accountant with experience in the U.S.A. than the other way around (particularly where the OP is located in PQ which has a different legal system not rooted in English common law).

It is completely absurd that this company is requiring the original documents, which is the root cause of this situation.

Lots of helpful people here, and we're all rooting for you!

I have been living in the Cincinnati area for 2 years now, but my roots trace further south. 

Most people want to set down roots and make a home in a nice community.