I don't believe Windchill itself will do this directly. I know of only two out-of-the-box ways. Either add a program to your drawing or use Model Check to add/sync the parameters. I believe there is a way you can hook into the actually Winchill Java processes, intercept check-in events, and do things prior to check-in, but this would be a custom application you would need to develop on your own.
We are attempting to use the drawing program approach, but it has it's issues as well. The primary ones being, a.) you can't pre-create the program in a template (at least not to sync identical parameters between the drawing and the model), b.) if you ever replace the main model in the drawing, the drawing program will not update itself to reflect that, and c.) you can only easily create a drawing program in an automated way (mapkey, etc.) if the drawing and it's parent model are the only things in session.