It'd be interesting to scale it up significantly. Maybe it would carry more weight? I don't know the legalities involved, but I've heard of some international mail order prescription drugs getting intercepted by the government. Are the laws more permissive when bringing prescriptions prescribed to the traveler, on their person?

Imagine a charter bus that takes a full load of people once per month from the US to Canada from regionally close cities (e.g. Chicago, Cleveland, Seattle, and New York) for insulin and other critical but expensive prescription drugs. The bus takes them to a pharmacy, everyone unloads and picks up their prescriptions, then loads back into the bus. Everything is called in, pre-arranged with the pharmacy for a streamlined operation.

It's a really stupid situation and possible solution that shouldn't be viable. Unfortunately, it probably could be done.