I think everything Tamara does is prompted by her desire for magic, whether that be for herself or for some other reason we have yet to learn. I think Greg and Tamara have two different agendas but they both think that kidnapping Henry is the solution to their problems.
Young Dylan does look very pirate-like there. We know he had to be apart of the crew at least for a short time because he learned how to sail the Jolly Roger, but the way Hook talked about the Lost Boys in Tallahassee would indicate that the relationship wasn’t adversarial.
[adrotate group="5"]
"He was a lot of things to me" "The only conclusion was love"