Unless this shop ride offers a sort of ride that other shops don't offer, I wouldn't bother WASP. It seems they aren't doing things to "give" back to the cycling community as a business.
I understand about the provincial license ...is that associated with a provincial cycling association for the insurance? I know the non-profit cycling advocacy group (VACC, now the HUB) has had to make sure they had overall insurance for its members.... I know this, because my partner negotiated the contract at different years for the VACC. But VACC's annual membership is pretty reasonable.

Which shop is this? I'm curious?

For the record, there is no B.C., Alberta nor Ontario legislation which requires cyclists to have license to bike. Of course bike couriers are different.