[Brian]

Welcome to the forums, BryanC!

I don't find Waiting For contexts all that useful in my workflow. Instead, the approach I use with situations like this is to make the action I put in OmniFocus de-emphasize the specific action of communicating in favor of the purpose of the interaction. Barring special circumstances where I must communicate via a specific method, I wouldn't file an "Email Bob to request X" action, in other words.

Instead, I file it as "Request X", then assign it to a context I've created for that person, so I know who's helping me with that request. If there is a reason why the communication must be of a specific form - like emailing them to establish a time/date the communication occurred - I put that info in the action title. ("Request X via email.")

Once I make the request - via email, or phone, or ask for it in a meeting, whatever - I use the start date to defer that action and get it off my active task list until I expect to hear back from them. (Optionally, you can edit the task name at this point; in practice, I don't tend to do this.)

Once that start date arrives, the "Request X" action reactivates and I pick up where I left off.

Your Mileage May Vary, of course, but it works for me. I hope that's helpful!