Theo first! Because his is easiest. He is going on epic adventures with Miles and Isobel, as long as she can stand the crazy. They will possibly be joining the circus. Or in Romania. Or... really wherever the impulse takes them. They will probably utterly lose track of time and so breaking it down by years really has no meaning.
Sherri... in the next year, she plans on going back to school to finish her degree. In five to ten years, she'll be working in a library, constantly pestering Joss to take better care of herself, and hopefully have met a man who she can see as something other than a friend and yet not be intimidated by and settle down and spawn some children to tell stories to. She'll likely visit Brian at least once a month, more if she can manage. His approval will be required before she will get married, and he will likely be Uncle Brian to any kids she has. Creepy Uncle Max is not welcome at family gatherings.