We did this as part of a larger community book (you want to talk about WORK!?)
but we went chronologically per family - from oldest to youngest. For instance we started with the oldest members. Steve and Sally Smith had three children, Joe, Jane and Sam. So we wrote about Steve and Sally first; introduced their children etc., then the next section started with Joe and his subsequent family - right down to the youngest leaf on his branch
. Then the next section started with Jane ran through her 'line' and so on. We had the titles in a larger font for the oldest on down to the youngest (We only had 5 or 6 generations though - so you might not be able to do this - but you could identify the person as Jane (Smith) Jones (always included the maiden name in brackets)- Generation TWO, just so if someone flipped open the book it could be easily identified where they fit in the grand scheme of things. It really is a work of love because it takes a LOT of planning and time and patience - but the result is priceless. Best of luck to you!