I tried both chevron reissue and jumbo in store and eventually went with the reissue although mine was the same distressed calf leather with black chain. You'll be able to tell if you tried both; I wasn't even thinking about the chevron reissue but once I tried it on, it was love at first sight! [emoji7]
Besides the softer leather, the other factor was the weight; the reissue is much lighter than the jumbo.
I'm not sure what size your reissue is (227?) but mine is 226 and it fits about the same amount of stuff as a jumbo can.