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Alston you may have to test this out for yourself. I Googled "Connecticut Health Insurance" from my computer in NJ. Your site came up as the #3 organic listing, but was found below the fold after three paid searches and seven local listings.
A rectangular map of Connecticut appeared in the right pane. It seems that Google selected a map area that best fit its rectangle, and chose to display locations north of West Haven - entirely omitting the more heavily populated cities of Bridgeport, Stamford, etc.
The seven local listings in the center pane were all found on this map. Your site outranks each of these listings, but is listed after them, below the fold. The only merit these sites seem to have is pure luck of the draw - the are located in the geography Google found convenient to display in it's map.
This was a standard search - not a places search.
And I count two SF agents (who sell only Time) and 1 Nationwide local listing, this is hardly the information I would want If I did a search as a consumer looking for health insurance in CT.
Also I did a search in TX and FL, for florida health insurance and texas health insurance, I assume that since no local listings showed up, that Google figures there are too many local listings for the bigger states to show places for broad search terms.