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I'm curious if you allow the project to enter actuals after the fact, then you can compare them to individuals/aggregate estimates so you know how biased your model/individuals/the organization is on these types of estimation efforts. You could give that as feedback as an additional service: "You're constantly overconfident on X type tasks..."

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Not at the moment. This is the dream, but it's statistically much harder than it seems!

For each task you have one distribution, and one sample. What's the likelihood that sample was actually from a different distribution?

Instinctively it feels easy to judge "your usually closer to the worst-case than the best-case" but mathematically it's not so straightforward, especially when the estimate doesn't include sick days, splitting time with other projects, etc, but both the projection and the reality do.

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