As Greg points out, managing documents with "triggered" retention rather
than pure "age" retention (while simultaneously combating space
constraints) is problematic for paper, but IMHO, less problematic with
electronic material.  I took from the original message that you cannot
generally determine an expiration date until it happens - this would be
a true "trigger" environment.  If you can predict, for the majority of
materials, a reasonably anticipated expiration date then you should at
least start managing the paper based on that date if you aren't already.
I'm not sure if you're having trouble identifying when the trigger
occurs or not, if so you'll need to establish a business process for
communicating that information to those in your organization that need
to know (i.e. You!).

If the materials were imaged and housed in a repository (such as a
contract management database, or perhaps a RM database), then the
process of application of retention based on trigger and grouping for
final disposition on those documents with the same destruction date will
require only actions in the database.  In the paper world, you'll have
to pull the boxes, pull the documents, re-box and/or send to the
shredder.  A much more labor intensive process than running a database
query.

Day-forward the process of scanning then shredding the paper and then
managing images shouldn't be any more labor intensive than your current
process - but it will be different.  The real cost of imaging will come
if you choose to image the backfile (those that already exist).

If imaging isn't an option, and you can't find more space to house them
onsite until expiration occurs, then you will continue to be in a
difficult (and costly) position.  Greg's suggestions should be very
helpful in this situation.

Good luck to you!
Julie
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