I've been reading them in the order in which they are placed in the book, but I think it will make more sense to read them in chronological order, although that will require some jumping around in the book.
I've gotten through about 30 of the documents already (including ones I'd read before), and I've noticed a few unsettling things: the notion that the participation in the liturgy called for by the Constitution rules out Mass in Latin, the notion that a Mass celebrated facing the people is a "truer" celebration (although it is not deemed absolutely necessary for participation), and repeated warnings and admonitions about the experimentation and unbridled creativity affecting the liturgy as early as 1965.