Obviously I know his narrative purpose is to speak thru music, and that the POINT is that he maintains his troubadour mystique. But I just wanted to entertain what the logistics of this character's life might look like.
Wikipedia says troubadours often stayed in one place under the patronage of a wealthy noble person. What if Emily hired him to keep tabs and try to communicate indirectly through a medium that she knows actually resonates with Lor and Rory? How many times have they walked past him after a Friday Night Dinner and he's singing something emotionally pointed at their exact situation? Or Trix definitely had the money and eccentricity to hire a musician to spy on her family members. Richard has ties to musicians/preformers, maybe this is one of his a capella buddies' kids?
Who IS this guy? Where does he go to sleep at night? How does he afford to live if he doesn't accept money from the townspeople, as patty said in the town meeting about him?
The troubadour mystique!!