-rubs hands- Let's do this.
I like where you were going with the stray thing for Jack and Maddie. I was thinking about that too as Jack is always taking in strays as well, also both human and animal. Maybe Jack gets a crate of pygmy puffs that she can't take on because her Jarvey keeps trying to eat them, and she has Maddie stop by to pick them up, or she takes them there. I love the idea with Charlie! Jack actually had two adopted kids (her bio is so in need of updating). Sunny, her niece, is 8, and Goose is 10. Perhaps Goose and Charlie could be friends as Goose is supposed to be going to Hogwarts but is going to get some really bad news about his condition (he's basically a squib because of a magical blood disease). The added discomfort because of Maddie's husband could be interesting. Jack isn't particularly close with anyone outside of her team, but she would have known him. Also, because of a Ministry mandate, Jack was married for a brief amount of time and began falling for her husband... and then he had to move to the US. There's a few parallels between the women that would be really fun.
Jack's not to be mothered though. haha. She won't take to that at all.
I'm actually trying to get something approved with Ducky that would work well into her getting the chance to mother him a bit. Finn and Wendy are the two girls that need the most plotting, and I love the idea of Wendy getting tea with her.
Also, with Casper as a 17 year old, it'd be really fun if one of my girls had a crush on him, which made it awkward to interact with Maddie. I'll have to investigate that more once I get to know him more.
Gabby will be sent off to investigate the Ilvermorny situation, so maybe he gets dispatched when Maddie decides to investigate too, throwing them together?