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I'm still playing around with this, but I really really really hate the idea of a context for each shopping destination. (Do I REALLY need a "hardware store" context?)

One thing I've been trying (which is what I did in Entourage) is setting up a task for each destination, and then putting the shopping list in the task's notes. The only downside with this is that errands to the same place from multiple projects aren't really supported.

Another option would be to just preface each shopping item with the store name/type, as in "Hardware Store: Pliers" and "Hardware Store: Hose".

Just ideas. For some reason the huge number of contexts strikes me as a PITA. I'd much rather have a simple "Errands" context I can scan when I'm heading out for the day.