Im kind of in the same situation like you, though not like you Im not using my reissue anymore. I have the same size like yours, mine just have the antique gold hardware and I only used it twice and I have it for 4 years. Its basically brand new. I kept it for the same reason that its an "Iconic bag" but recently I realized life is too short and if I don't enjoy something, I would have to let go and spend it on something that I really love which would be boy bags and mini flaps. They're more practical for me. I get more mileage on them. So rather than keeping a bag just for the sake of having it because it's supposed to be what others think looks great, I would get what I feel is best for me. That's just my opinion. HTH.
ETA: Reading again your post, it seems like you really still love your reissue so in this case, you have no choice but to just save up some money for a boy bag. If Im still getting a lot of use from my reissue, there is no way I will consider selling it for sure.