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Another approach which would address your situation, instead of multiple contexts, is to be able to add metadata to OF's tasks.

For example, if you could add a column for Person, and be able to view all instances of a person across contexts, I think it would address your need.

Or if there was tagging, you could tag all tasks that involve a person, whether you were waiting on them or you needed to respond to them, or have an agenda with a committee that they were on, and then view all tasks which have their tag.

As long as it's easy to enter and easy to sort by for viewing, I would take any kind of metadata solution.
I would also be open to some kind of metadata solution although it would be important obviously for me to be able to use it to implement multiple contexts. I haven't given it much thought. I think other apps implement this as you say by being able to add columns, or through use of keywords, or through tags.

I played around with Ecco Pro 4 last night (anyone remember that?). It's probably the most flexible "PIM" ever created in that it allows definition of additional columns, and allows one to be able to choose multiple values for a column.

I could use it to implement GTD, or could create a MS Access database, or use one of my other tools. I probably could even use Omni Outliner in some way because it allows one to add columns.

However, OF is too powerful in many other ways for me to give it up so I may have to compromise in some way. The most pure way for me would be to have a preference set to allow multiple contexts. As I played with Ecco Pro 4 last night I could see what the UI might look like in OF when selecting multiple contexts.

I realize I might not get multiple contexts, but I always feel good when I put forth the effort to try to get a good feature -- not only for me but for the tool itself and its future. If multiple contexts aren't implemented I will find a workaround that works best for me given whatever features are available at any given time. Perhaps meta data or something similar will provide a better workaround in the future if they are added.

I totally agree with you about multiple contexts. The way I work they are essential! I emailed support back in August requesting this feature.

For example I would naturally add the activity "Ask my friend Mario to recommend a good accountant" under the contexts "Phone" and "Mario". If I'm waiting for the bus and I have a few minutes to make phone calls I'll switch to the "Phone" context and see the activity or if Mario calls me I can switch to the "Mario" context and see the activity. Contexts are about opportunity and if I didn't have it in both contexts I would have missed the opportunity in one of the scenarios.

An important concept in GTD (I'm not stuck on GTD btw) is that you have to trust your system so nothing will slip through the cracks otherwise your mind cannot completely let go of the task and it stays in your brain's RAM. If I bump into Mario (I'm hoping OF will run on the iPhone at some point) and I think there's something I need to ask him that might be buried with my many other tasks in some unknown context I'll lose trust in the system.

I'm a long time user of ECCO Pro and I've been assigning multiple contexts to my tasks for years. Even though support for the product was discontinued in 1997 it's still very relevant today and was well ahead of it's time. OmniFocus is also an amazing product and will be even better in my opinion if they support multiple contexts.

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