Another 'tool' for the box loadout might be a couple of lists. You are building this for the purpose of teaching and demonstrations. I'd guess that you will do some sort of practice for the course or demo session, or at least a walk-through. Go through your lesson plan and set the tools you use out on a cleared bench as you get through using them. If you are doing a tour with several different events scheduled before returning to the shop work off of the pile of benched tools adding those you don't have out already as needed. That should give you your minimum load.
A photo or check list of tools for a given course or demonstration could minimize both the load as well the 'rats, forgot it on the bench' items.
Presumably the traveling box is not a separate tool collection but is loaded from the shop collection when you head out. Although it would be a fine 'reason' (excuse?) to add more to the collection. :)
I rather like the idea of the campaign chest approach too. A collapsible gurney might not be a bad idea either. Remember to bring your back home in one piece, as well the box and tools in good shape, eh?
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