You may be able to set a simple board schematic to enter and provide an picture of the desired layout. Do a spec of the desired pad sizes, hole sizes, track sizes. Possibly use non-standard values so that no package gets an advantage with pad sizes that already match the spec.
Then ask for volunteers to do screen capture videos as they enter the schematic, layout the board, perhaps try autorouting in packages they know, clean up the layout. etc.
How well the boards are done is not the issue, it is just seeing how easy it is to do the steps. It would have to be kept simple, so that a video is less then 30 minutes. Perhaps also one video of making a schematic part, and one of making a PCB layout part. Require that the schematic gets changes and the PCB has to be updated.
It wouldn't be comprehensive, but could be a good starting point for getting a feel for a new package. It would be really easy to bag a package for missing a feature you are used to, when that package just doesn't need that feature at all. Or bag an unfamiliar package for being slow and clumsy, when a video may show that used properly, it is fast and efficient.
Just as an example, I have never even touched gEDA. It sounds like the least friendly and unintuitive package to get started with, but there are some people who swear by it. If someone went to the gEDA forums and asked, they might find an expert volunteer and that would be interesting.
Richard.