Well the nice thing about digital is its so much more interoperable than analog.
Digital radios can do analog, older analog radios can't do digital, making them poor for interoperability.
If a town, (lets say Milford) has encryption they can still hear units (say Stratford) trying to contact them in digital clear, and the Milford units can switch over to their clear mode and answer Stratford in the clear and keep the incident clear until its resolved, perfect interoperability. So to be clear, an out of town unit can key up and call on a digital channel in the clear and the units that are on that channel encrypted will hear them, to talk back they just change to clear and everyone hears everyone. You could also set the channel up Mix-Mode and make it possible for analog units to contact the encrypted units and the encrypted units can then change to the analog channel for the incident, making a Digital encrypted system even more interoperable.
If I just put my scanner-head hat on I still love digital, it sounds better, and better audio for a greater distance. Down side is encryption is quick, easy and with Motorola comes free with all new APX radios, it is only 40 bit ADP and not up to federal standards but in the industry its called Anti-Scanner encryption.
If west haven goes digital with out encryption, I would say its a huge win for scanner heads as its going to sound great