His whole first term on the Barge happened on one day in 3021, the year his first daughter was born, while he was coming home from accompanying Frodo to the Grey Havens.
In year 21, he and his wife and his oldest daughter travel to Gondor for a year. I'm tempted to pull him from here? Invent a problem for him to solve so he has something to want a deal for. His wife is pregnant when they get to Gondor, and his daughter falls in love with a hobbit they met on the way home and gets married.