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I am trying to find some software that allows the following workflow:

  1. Create a wbs with effort.
  2. Plot wbs items onto a Gantt chart to see when items should/could be completed by and build a schedule.
  3. Update the items with real world data for how long a task took, and progress and rebuild the schedule to account for this (so push items back).

This should hopefully allow me to have some view of how long the project should take and allow a post mortem at the end to assess my estimation skills.

Although one piece of software may not be applicable, I'm open to combinations. Most importantly is the ability to enter in the real world numbers next to the estimates for evaluation purposes.

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Check out the evidence based scheduling from Fogbugz:

http://www.fogcreek.com/fogbugz/evidence-based-scheduling/

  • Evidence based scheduling was precisely what I was after. I'm evaluating fogbugz now. Thanks for the article on evidence based scheduling, it really helped my decision. – Clockwork Ant Jul 10 '12 at 9:49
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There are lots of software products that could fit your needs, as what you need is basically the ABC of a project management software. Maybe you should first have a look at this Wikipedia article: Comparison of project-management software

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There are many different software packages that will do what you are looking for. You could use good old Microsoft Project to do all of that. You could even use Microsoft Excel if you wanted, the Gantt chart would just be a little more work.

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