So I assume that the geodatabases, the address locators, and such are all the sticking points in terms of the "products" of ArcMap. I suspect that sometimes their software dips into that specific version of arcpy, as well.

Until the vendor hops, we cannot hop. It's a problem that will be eventually fixed, but I bring it up because many people here at HN think of greenfield development often, and also in industries where tons of iteration are met with approval.