The Courant has the same problem.
Personally I think the Torrington Register Paper is better than the New Haven variant of the Register and their present model works better in the vacuum of the 5th. We don't have a decent independent press in Litchfield County or even decent lcoal coverage at all outside of AOL Patch and the Register and several other small newspapers.
Barnes and Noble is a case study: they had to seperate their digital into a seperate division to give them the freedom to budget and innovate. The legacy business (the stores and warehouse) are a different operation with different budget and goals. The earlier attempts to create synergies between the two created more problems than they solved.
I predict in 5 years someone consolidates the statewide news here. HuffPo CT or ThunderDome or whatever. That leaves the cities large enough to support an independent with investigative reporting and some county-wide (or District-wide) initiatives like the Register and Journal Inquirer and the Day that share content with their local Patch crowd.