CGAL's docs are pretty good but there's a fair amount they assume you're know. I bought a copy of CGAL Arrangements and Their Applications and found it to be very helpful for filling in those gaps and understanding the architecture.
With a better understanding of arrangements, I started trying to implement the OBB-based Subdivision algorithm described in Procedural Generation of Parcels in Urban Modeling. It's looking promising but I still need to implement the checks that a lot's area is within a range and that it has a certain amount of street access.
In the process I figured out how to get my straight skeleton block division working for shapes with holes: