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I've defined and redefined my contexts a few times. My problem is that I find that when I work on my computer, I prefer a 'flatter' list of contexts because I can very easily pick and choose the contexts I want to see together (command-click) and working on the iphone I prefer a more nested system. I started out more nested, then got away from the iphone and 'flattened' my contexts. With the 1.1 release, I'm back to using my iphone more and re-nested them. I can still do the command-click thing if my sidebar is expanded.

Another change I have made revolves around my 'desk' actions. Again, I think I had them split when I had a top level of contexts split into 'work' and 'home'. Then when I flattened the contexts, it didn't make much sense to have them split (because most of the desk-type items, even if they are work related, I can do at home. And it seemed artificial to have them separate when, if I was sitting at my desk I could just as easily do work-task-A or home-task-B. But in my re-nesting, I realized I always mentally choose which I'm going to do (a work task vs. a home task) and I'm happier with them split.

Just my two cents.