Great pics of both bags. I am trying to decide between the jumbo flap and the GST so i empathize with you and your decision process. Enjoy the pre-loved GST, it does look very good on you.
nightshade, I think you should really keep the metallic black reissue. While i love the jumbo caviar flap myself, i think the reissue looks stunning on you! it's a keeper. i also love how the GST looks on you as well. I love your sense of style.