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This sounds like a feature request three sets of start and end dates, specifically optimistic, expected, and pessimistic dates for task completion. I'll add your vote for this in our database.

We don't have this feature now and the only possible workaround I can think of is to enter three tasks and group them. Set each task with either the optimistic, expected, or pessimistic dates and color-code them differently if you want. Not perfect by any means, but it could be presentable on paper to show the higher ups the three possible outcomes of your project.