Saying that your future estimates will improve based on your last ones, is like saying you have more chances of winning the lottery if you lost some games before.
We have third parties building portions of our systems and for some of them I can estimate reasonably well their actual net duration because I've had a lot of experience with them, and they've been fairly consistent.
But there are others where there's a wide range, so I think it boils down to whether you can spot a pattern or not.