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Say you have a program that currently functions the way it is supposed to. The application has very poor code behind it, eats up a lot of memory, is unscalable and would take major rewriting to implement any changes in functionality.
At what point does refactoring become less logical then a total rebuild?
Joel wrote a nice essay about this very topic:
Things You Should Never Do, Part 1
The key lesson I got from this is that although the old code is horrible, hurts your eyes and your aesthetic sense, there’s a pretty good chance that a lot of that code is patching undocumented errors and problems. Ie., it has a lot of domain knowledge embedded in it and it will be difficult or impossible for you to replicate it. You’ll constantly be hitting against bugs-of-omission.
A book I found immensely useful is Working Effectively With Legacy Code by Michael C. Feathers. It offers strategies and methods for approaching even truly ugly legacy code.