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While some things are multiple contexts some can just be handled with tags. There are many things that can be completed without other's involvement, say expense report, but if I have a tag for Susan the company accountant and I am sitting with her, I could filter and pull up related tasks (the two items I am not sure will be approved in expenses makes a this a much quicker task and done in one pass).

I also have contextual conundrums as I have a task for a face-to-face meeting with a friend, who lives in San Francisco. But, I also run into him at some conferences as well as when he floats through the town where I live. If I am planning a trip to SF the note to email my friend to set up a face-to-face and put it on the schedule is needed. For a while I had this in SF trips context, but not in conference related tasks where he was.

While OmniFocus has location context having another "person" context would help as well. Tying this to their entry in address book would be quite nice (the simple mapping names to address cards like VooDoo Pad does is really nice). When adding a person and seeing latest interactions with them (similar to the review with calendar view slated for OF2 would be quite helpful).

I really like the main multiple context filters outlined in the "what should be do..." in Brian's post above.