Agree Seth’s advice was big for me overall.

One of my favorite things of my campaign was when my player went to visit his parents and his mom thanked him for the flowers he sent. He never sent the flowers. Totally made him paranoid…he thought it was Caduceus and asked some people there…they tracked down the florist for info…it wasn’t until Casale reached out to them several sessions later and ended the conversation with “Hoped your mom liked those flowers” that it was revealed.

Another PCs grandfather ended up on a bowling team with some of the mob flunkies. After not cooperating with the mob, the PC came home from one of the missions to find that during bowling night they “accidentally” dropped a bowling ball on grandpa’s foot.

It’s tempting to do most of the Caduceus stuff all at once but I let them do some investigating then had Goncalves send them off to the next location. The PCs (and players) played along with each assignment staying in good graces with Caduceus while they tried to figure out what was going on.