I suppose it depends on how important listening to Westmoreland Sheriff's Office is to you. Personally, I hardly ever listen to law enforcement, so it probably wouldn't matter much to me.
Do you come to the Richmond area much, where a lot of digital is being used? If so, you might think about it.
Keep in mind though, that more and more places are going to be going digital, so it might help to have a digital capabable scanner. But, as rural as the Neck is, I wouldn't expect this to happen overnight!