How will Blackmailer work? Not being able to talk in a discussion-heavy game doesn't really work out.
What can a "demand" be for gypsy?
What's the purpose of the Gossip? I understand it on a mafia role, but this is a townie.
I don't see how Matchmaker can work as a town role. Can you explain in what situations this would be good for town?
Am I going overboard with all these questions?