Earlier quoted context omitted.
But you have to include 'estimates', which ruins everything (in non-trivial cases, yadda, yadda).
Estimating is my Achilles heel. Always has been. I'm way too optimistic. My workaround was to do jelly bean estimating. Get guesses from everyone, then use the average. Worked surprisingly well. We did other things to meet that target date, honor that estimate, of course. But that's a longer story.
In my practical experience, I multiply the amount gathered from the previous statement by two to have sufficient negotiation space for people 'higher up the chain' who have no idea about anything of this and simply pull estimates out of thin air or their rear without any proper experience except "previous time it was xxx so it should be the same" (which it almost always is not).
edit: I prefer to have some time left on larger projects to avoid overrunning, even though that might be common practice. Usually though time is cut short due to delivery constraints or selling a product before asking the development and you get the 'wasn't it done yet?' speech.