For Alex and Rob and Sean:
With the new one-file-per-webwork representations setup, it is now possible to use the cli's caching mechanism we use for latex-image, prefigure, asymptote, and sageplot. I don't think that writing the webwork representations for each problem is that time intensive though, so I don't know if it is worth the bother.
What we (will do) now is collect a hash of the entire collection of webwork questions to see if any of them have changed. If even one has, then we would regenerate all of them. This will also happen if any of the individual representation files is missing: all the webwork gets regenerated.
If we moved to the caching strategy used for images, then when regenerating all of the representation files, we would check whether an individual file has already been generated, and if it has, copy it from the .cache folder instead of recreating it from the server.
I realize that we would also need to do this for any generated images or pg code.
So would this one time effort by me make this significantly better for folks with project that have lots of webwork questions?