[Journey]

If it were me, I wouldn't have a PhotoShop context if it didn't group items in a way that would be useful for efficient processing. In the case of using Photoshop for different projects, what is the economy of scale there? It doesn't seem like there would be one unless you had to walk to a different location or sign up for a time to use a specific PC for PhotoShop, or call PhotoShop support to get questions answered that pertain to different projects and you wanted to get it all done in one phone call.

For project management, I would spend most of my time in Project mode, but go to Context mode whenever I think things might be grouped in a useful way, and then I'd be looking at specific contexts. Knowing that all activities associated with a context would be there is important, which is why being able to assign an activity to multiple contexts is important -- because when you look at a context you don't have to wonder whether something was categorized somewhere else in a "context hierarchy".

An example that you might find helpful as an IT manager might be to have a context for the different people you may need to talk to in your organization. If you need to consult someone for an activity, you can assign that activity to a context for that person. If Omni Focus allowed multiple contexts, and your question could be answered by Bob or Barb, you could assign the activity to both "Bob" and "Barb" contexts. That way when you are about to meet with or call "Bob" or "Barb", the activity will show up there (and with multiple contexts, the activity could also show up under "Phone").

When I was a project leader at a corporation and / or worked on many different IT projects, at times I interacted with the same person from many different roles or projects. Using contexts in that way would have been helpful but alas such tools weren't available at that time (I haven't worked in IT since 2001).

This is an example in which multiple contexts per action item AND a context hierarchy would be helpful. Usually the number of people I interacted with in my IT position were the people on the project teams, technical staff, and users. I could create a People context and then sub contexts by group. Then when an activity came up in which I needed to phone "Barb" or "Bob" I could add the activity to the Person:Bob, Person:Barb, and Phone contexts.

Feel free to follow up with any other questions you have.

I don't know how anyone could manage something very complex without multiple contexts / action, but I guess if a person spent a lot of time trying to define an exclusive-hierarchy and was very diligent in following it, and didn't have to refine it later, then there is a slight possbility it might work. (and hopefully you'd never have to explain it to someone later on)