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Thanks for everyone's patience in helping me figure this out. I'm loving OmniFocus so far.

Can you create additional "Waiting" contexts underneath "Waiting"? Like "Waiting: Rob" for example? That worked easily under "Mac," but it doesn't seem to want to do it for me under "Waiting."
Yes, you can create nested contexts like the one you propose. If you select the prospective parent context in the sidebar, then click the + at the bottom left, it will create a new context nested just beneath the parent. Or, if you've already created the context somewhere else, select it in the sidebar and drag and drop it on the desired parent. Once you've got it at the right level in the hierarchy, you can adjust the position with control-apple-uparrow and control-apple-downarrow.
That does not seem to make it nested for me. It places it on the same level as the "waiting" list above, not like at all the ones for "Mac."
Sorry, my answer doesn't apply for all cases, but it did for my test case!

If you don't have any nested items under the prospective parent, it doesn't make the new one nested. However, all is not lost; after you edit the name, just press cmd-] or do Edit->Outlining->Indent to make it be a nested item. Or drag and drop it on the parent, as I suggested.
Works great. Thanks...

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