What are the pitfalls of document management in the digital age? Let me count the ways:
 

• statutes (e.g., SOX) may tell you how long you have to retain documents
  (five years past an audit, e.g.), but if not you have to decide what
  your policy is;
• you can violate that policy (inadvertently, we assume, but tell it
  to the judge) both by destroying things too early and by retaining
  things too long;
• water-cooler conversations that once evanesced into thin air now
  tend to be searchable e-mail threads (see:  Henry Blodgett, Jack
  Grubman);
• meta-data can reveal the genealogical history of a document’s changes
  (Slashdot first revealed that the
  complaint in SCO’s Linux copyright-infringement lawsuit was originally
  drafted not against AutoZone and DaimlerChrysler);
• backup tapes are typically written and re-written over, and previous
  data may be recoverable;
• what do Fed. Rules of Evidence §§1,002 and 1,003 dealing
  with "Requirement of Original" and "Admissibility of Duplicates" really
  mean in this day and age? (a metaphysical question, if you ask me);
• and on and on it goes.

I’m not a litigator, much less a fan of the medieval rules of evidence,
but this lays it out with reasonable succinctness.