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So if I understand what you're trying to do, you want there to be some period of delay between sending the proposal to someone and when you follow up with them.

Rather than a waiting-for context, I tend to use start dates to accomplish this. check off "Send Proposal", and when the subsequent action appears, just set the start date for "next week" or whatever works for your purposes.

A start date in the future will also cause the subsequent actions to become unavailable, with the added benefit that when that start date comes, the actions will automatically re-appear.

Does that help at all?