>> all the meetings you have to attend to explain how far behind you are with the project, usually repeating the same thing to several levels of hierarchy at different times
At least you're explaining it to DIFFERENT groups of people.
In a small company, we had to explain to the same group of people in charge of different projects in different meetings multiple times, and get chew out for the same reasons multiple times, because of the people in charge compartmentalize their thoughts and believes that we're working on each of their project full time (despite the same group of people having sit in for each project meeting and hearing the same explanation) when in reality we've been ordered to work on multiple projects concurrently.
Take the due date, multiply by an incompetence multiplier of (minimum) 2.3, and add five years. I'm 22 and I've been in the work force for a year now. I can't think of a single project that has been completed in that time...
Fortunately, I learned how to deal with the due date problem early in my career. First I would carefully estimate how long it would take to do the job. Next I would add a percentage for the problems that always arise over the course of a project, usually 20% to 30%. Finally I would take that number, double it, and schedule accordingly.