Why does Maddy have the inclination to con Drew into girls clothing? Every time a Con is scheduled, and they attend, Maddy tricks Drew into a female character's clothing. One day she'll get her feelings rightly hurt when someone tells her no and means it.

The girl at the Con looking in has understandable trust issues, possibly from being deceived and/or disappointed too many times. So it's understandable when Drew offered the pass to the Con, she was skeptical. At the same time, Drew was doing something good for someone else. Only asking that she accept the pass.

What happen to Drew's hand? Did it happen on the flight, before the flight or after the flight? Will this affect his/her riding?

Change isn't always easy, whether the change is wanted or not. Drew has little choice in her change, since she now has an active set of female organs. Drew was never a boy at birth, just thought to be one because of Herbert. Being treated as a boy for fifteen years is hard to get over when it's known what lies ahead, and a possible change in racing. It will take time for Gaby to mentally adjust to the new body housing that mentality.