You ask an interesting computer science question (that's unrelated to Cocoa).
   
  Surely the following sequence of words would produce Word[1-9]{1,2} instead 
of Word[0-9]{1,2} because there is no representative 0 in the sample ?
   
  "Word1"
"Word2"
"Word5"
"Word8"
"Word11"
"Word19"
"Word23"
"Word45"
"Word77"

  Anyway, I think this is an unsolvable problem, and I might start with an 
attempted proof of its unsolvability rather than a solution.  Lots of 
artificial intelligence and/or statistical pattern recognition could be applied 
to achieve reasonable results in general cases. If you have specific cases like 
letters followed by numbers you might use a lexer and parser like flex/bison.
   
  Have you considered a "perfect hash" ?  What are you really trying to achieve 
?
  http://en.wikipedia.org/wiki/Perfect_hash_function
  http://www.nist.gov/dads/HTML/minimalPerfectHash.html
   
   
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