I'd love to play out scenes with both Edward and Jake. Messed up family dynamics are SUCH fun to play, possibly my favorite type of plot. I do think Mary will be involved in a few charitable organizations, so maybe she and Lily will meet up at some point. Kirley sounds like the sort I would get along with famously, but I agree I can't seem him naturally crossing paths with either of them.
Bill/Dawlish mutual antagonism sounds like great fun! I like that it will be due to their personalities clashing, since ideology wise they do seem to roughly match up. I sense many disapproving glances and exasperated sighs in Bill's future...