I rewrote a good portion of KonaKart in Flex. I have a checkout page that allows users to ship various items to different addresses. It also allows users to select a single shipping address from their address book and apply it to the entire order. I'd be happy to post the code, but it's all actionscript/c# based. It's definitely doable. The only thing I have yet to do is actually update the handler to deal with multiple shipping addresses. Not quite sure how to do it properly yet.