In each season there is a variety in the nature of the leather and different people like different qualities in the leather. A 2006 bag would be chevre (goat) while the 2008 bag would be agneau (lamb). Some people believe chevre is a superior leather but this is by no means unanimous. The City is a more popular bag style but there are a lot of Twiggy fans out there as well. They both hold about the same amount. I have not dealt with Corey but I gather she is very helpful. If there are particular characteristics you are looking for in the leather, i.e. thick or thin, veiny or not veiny, distressed or not distressed she can help you with your decision. If it was me....for the same money I would probably go with the marine Twiggy mostly because it is in better condition and would probably stay looking good because of its darker colour.