[jellifeesh]

I don't use context in a strict sense, in fact, I care little about contexts. So for me if a specific task needs to be completed by someone other than myself, then I assign their name as the context. I think maybe this is awkward for you as you still want to use context in the spirit of "GTD" aka David Allen approach? But if you delegate, who cares what your context is - you just care that the task is completed.

There could be a better way to be sure to accomodate delegation. However, Omnifocus is not "GTD" and I really don't want it to be. Its a general framework that is probably far from perfect for everyone but its simple and flexible enough to be implemented in anybody's work-flow. So a better delegation would be useful for some but software bloat for others that don't need this feature??