What if I’m shopping at a grocery store or pharmacy and bring OTC items and non-OTC items to the register. Do I have to do two transactions, one for OTC items and one for non-OTC items?

No, you don’t have to split up the transaction.  For example, a member goes to Shaw’s and bring a bottle of wine and a bottle of aspirin.  The member will present the Flex Card first, and the OTC purse will be debited for just the bottle of aspirin.  The member will then need to pay for the bottle of wine with another form of tender.