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If you enjoy using it and use it often, wait to sell. You never know. Prices keep going up and you may get more for your bag down the road, if it's in similar condition. And you may end up affording a new colorful one later anyway! If there isn't a bag you're dying for now to replace the black one, don't accept an offer. Even if it seems good.
In the same situation, I was thinking of selling my black jumbo, for an excellent price, in order to purchase a more fancy flap. We might use the black but agree it doesn't exactly set hearts aflutter. However, the prices now are STUPID. I wouldn't repurchase if I were to sell. So I've decided to hold on to it for a while longer, there will always be a buyer. Also, coloured flaps are beautiful, but I rarely use mine. With regards to Birkin v Flap, what have you been wanting the most? Don't get distracted by a good Birkin price if thats the case, don't feel pressure to buy. I was feeling indecisive as you seem to be, I've personally decided to take a step back and not buy or sell until I am certain.Ok so something new has come up! I have the opportunity to buy an Hermes Birkin for a very good price. If I do it means I wont be able to get a colored flap for a whileBut I so do want one as well (greedy !!). The options are to let go of the Birkin and get the colored flap ... or get Birkin and put colored CF on hold.... OR Sell the Chanel Black Medium and get both the Birkin and Colored flap!! What do you think?? So confused!