I haven't fully decided if they will all go up at once, but that seems likely. Jill and a surprise mystery guest have chapter 1s to finish, but those may not be fully over before chapter 2 maps are done. None of you are within 3 of each other to start, so the only reason to wait is so you guys don't get too far ahead.
Chapter 1 summaries are... Up to you guys, honestly. Everyone's chapter 1 is very similar, they should diverge from this point, however.