My favourite part of making characters is kind of hard to say. I guess I just like trying to come up with ways that different characters could be made cute and likable. I'd love to have it so people could know more about the characters, it's just too bad that it takes time to figure out how to present finding out more about them in a way that's entertaining. But oh well, I'll get there one day.
I can give some ideas of course.
The Raven honestly seems like the type of guy to be a switch. I don't know why. He seems really chill at times but can be very serious. I actually can see an interaction after the Gator interaction going something like this.
You know how he's a wanted man right? Well perhaps he goes missing at some point after you gain enough abilities from him and after the Gator scene. You don't think too much about it... at least until you are woken up by Mitch, the admiral, and the Gator who come to your house for help. You quickly find out that the Raven was captured and put in a prison. Of course there are a few ways to go about this. One is breaking him out, which could get you in trouble if you aren't careful. The second is to visit him in prison and see if you can vouch for him in court. The most effective is to get the admiral the funds to basically put the Raven under his jurisdiction and house arrest with the Admiral which none of the crew except for the Raven mind. Of course he is quite adamant that he feels he deserves to be imprisoned as he was involved in an incident that you need to press him for more information on.
Of course his story might be entirely different but that is just a single possibility.