Yes, the questions could be more direct, but surely, if they think the money should be spent, then, by definition, they expect the races to be run, and want that to happen.
I think you are rtight about press launches etc, as they are all preaching to the converted. We need to get over to those who neither care one way nor the other, what's in it for them, and get them to know the competitotrs, so they don't see them as outsiders who arrive, cause mayhem and leave.
When managing change it is always those who are indifferent who carry the change forward (usually about 60%), driven by the enthusiasts (15%)... maybe as well as a Safety Officer, we need a Change Manager!
My only worry about the school twinning exercise would be if something happens to their rider. That could be counter productive, and damaging for the youngsters? The Scouts are obviously involved, so how about starting there? A knowledge badge about the TT?