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Simpler to just put a start date on the waiting task to reactivate at the time you wish to take action. No need to change context unless you specifically want a list of things on which you are waiting. If you have a request for Bob to provide you with some document, in your Agenda:Bob context with a start date in the future, it does not appear in your active list, but blocks progress in sequential project or action group, automatically comes to life if Bob doesn't respond, and can be easily found when you run into Bob by looking at his context, which you would be doing anyhow.

While OF does come with the Waiting context on hold out of the box, I haven't heard of any Omni employees who actually use it that way. I have gone back and forth over the 5+ years, but have used the approach above for the last 3 years and don't anticipate further switching. I do use some Waiting contexts, but they are descriptive in nature, so I know whether I'm waiting for an email, a FedEx parcel, etc.