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That's an interesting way of doing it, and it makes a great deal of sense.

I don't think there is a way of doing what it is you are wanting.

To rephrase:
you want to set a context status to on hold
you want to view your contexts using active and not remaining filter?
and you want the on hold context to be visible while filtering contexts by active.

I can tell you how I work with waiting for.
I have a waiting for context set to Active
I have my context filter set to Active
I have my Show Actions With Status filter set to Active

When I have a waiting for item, I give it a start date in the future.
In the context view, the waiting for context does not appear because the action that is in that context is in the future.
When the action becomes available, the waiting for context appears.
I then process actions in the waiting for context, completing or moving the start date into the future.

If I need to see all waiting for actions.
I change the Show Actions With Status filter to remaining. I can then see all the actions in the waiting for.

I like the idea of having the waiting for context on hold. Maybe I'll fool around with that.