I would research his cases to understand what he "specifically" did.  

Anywhere in Naperville or in a specific area?

While Boulder specifically might be out of your range there are some other spots close enough to make it work.

They may have a market or two that are eager to insure a specific area and have much lower rates than the others.

I dont know of any specific local meet ups for OOS investing but there are a lot of different REI meet ups in the city.

That's what an agent does in the process & should be the only thing they do.I might catch grief for the last comment but whenever you invest & are unsure of something you should employ the person trained in the specific area.

I personally hate when people pull comps strictly based on a specific distance.

Hello, I was wondering if someone had any recommendations for a good general contractor for demolishing a brick stoop and rebuilding a concrete stoop in its place in the Northern Suburbs (Wilmette specifically). 

Hello,I was wondering if someone had any recommendations for a good general contractor for demolishing a brick stoop and rebuilding a concrete stoop in its place in the Northern Suburbs (Wilmette specifically).

Borrowers should always keep their specific situation in mind when discussing terms with their lender.