Bobray, revo looks awesome, and ultimately I guess thats what I’ll end up using when I find the time to look into it further.
Susan, your idea was super, being able to use tags in ditto is pretty awesome. I got the ditto/tv/checkboxes working in just a few quick minutes but unfortunately I then realized I need the structure to be laid out in such a way so Wayfinder can construct menus/submenus and make active links, which looked to be a nightmare with the way I had structured it all for Ditto.
The final solution (which is now 90% complete and looks like it’ll work really nicely) was to have a container for all the product resources. A second container held the product catagories on the first level (also as containers) and under each relevant container a weblink is created to point to the relevant product in the product container. These weblinks are automatically created (and deleted) using the DB API and a simple onDocFormSave plugin, which reads the product templates category checkboxes with are selected/deselected depending on which categories the products should appear in. Using weblinks means the structure is kept tidy for Wayfinder.
Thanks for the awesome help and ideas. You guys are so knowledgeable on modX - it would be extremely difficult to grasp some of these ideas without help from the fantastic modX community.