Thanks for the answers.
My main problem is that I have scripting and programming experience, but no micro-controller experience.
The design at DerbyTimer lacks some features I would like to see developed, but I am unsure what would be the least painful, but hopefully feasible, way to duplicate the functionality of that design and then develop it more.
The board seems to lack the required number of I/O to implement the &-segment displays as the DerbyTimer does, but I figured that could be worked around by using a de/multiplexer.
Even if I were to get more into the lower level programming of the controller, the Diecimila board does look like a nice platform to start with.
Sorry for poor chip, terminology. My IC experience dates back quite a few years.