Uff. Difficult question, but certainly ripe for discussion.

I can pull out #dotcolors as an example. I'm currently planning a rewrite for it since I like the product idea, but the code base was pretty experimental and the structure has just gotten. Uh. Wild.

Generally I tend to refactor if I'm happy with the overall structure of the project. Then I just pick out single features and refactor that. On the other hand when I feel that a codebase becomes confusing and unmanageable for me I tend to be pretty harsh with rewriting.

That sounds about right.