In the 2001 mappack at least, in the folder "hl2_2001" there is a file called "Maps list.txt"
This shows you the order in which the maps go in.
None of the maps in the 2001 mappack are necessarily "broken", however valve does leave a lot of maps somewhat incomplete due to moving on to new ideas and such.
I would say that the most content filled maps of that era would be the story line maps.