Before assuming everything is disheveled and that there is no real
organization, you may want to spend a little time looking at the contents
"forensically".

Your predecessor may have been someone working on their PhD, and the items
you're looking for may be the result of their work... everything is "Piled
High and Deep".  

The piles may be "organized" , albeit loosely, by subject or system AND they
may be reverse chronological.  If you're DDOT, there may be some related to
rail, some to roads, some to transit... it's possible that you just don't
see it yet.  Thumb through the piles and see if they are in some date order-
if they are, you'll likely want to at least make sure that remains
consistent for when you start your deep dig.

If your predecessor is still available, it might be good to try to invite
them back with an invitation for lunch or dinner, and ask for a quick tour
of the facility to see if you can get some insights into what you're looking
at.  If not, there is likely a long-time veteran of DDOT on-site that might
see something you're overlooking who could offer some assistance.  And
whatever you do, don't ridicule or critique their "system" =)

Whatever you do, take lots of pictures and keep an index of what each
exposure represents (location in room, adjacent to xyz, etc) and label the
boxes accordingly so when the holdings arrive at the new location you'll at
least know where they were when you started... believe it or not, those
'adjacencies' may have some meaning.

Good luck!

Larry
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