I offered to do this in Wallingford and Old Saybrook. Their sentiment was the same.
In Old Saybrook they actually told me "The Chief wouldn't appreciate being educated about the laws by a citizen.".
You can certainly try, and I am sure your mileage will vary, but I wouldn't get your hopes up. It is simply not that easy. You will hear the most amazing rhetoric from some LEOs.
"I would never want to OC, I CC."
"Why you want to do that?"
"What is open carry?"
"Someone will take it away from you!"
The other issue I see is that I rarely spend time in my hometown, but I spend a ton of time in other towns, often all over the state. I cannot ask permission of every Chief, and I certainly shouldn't have to. People have also proposed asking permission from property owners and business owners, but this falls under the same problems. It is making a problem where there wasn't likely to be one before.
In CT, most people just don't notice. The ones that do mostly don't care.
I have been OCing since April of 2010 and I had a police situation in May and one in October. It just isn't that common.