Personally, I wouldn’t have sold BAG #2: Chanel 19 Black Medium/Regular if I only had it for 3 months. It’s just not long enough to generate any profits to be considered as an investment. Things aren’t an investment if they aren’t generating a return for me. In total, with all the bags OP listed, that’s almost $4000 loss. That’s a LOT of money (at least to me).
I have sold bags in the past (not Chanel), and it’s always at a loss. I don’t consider my bags as investments that give me financial gains. This is also why I am almost at “purse peace” with my collection. Throughout these years of bag buying, it helps me realized what works for me and what doesn’t. Hence, minimize loss.
Overall, I don’t consider any luxury goods as investments - bags, fine jewellery, ready to wear. 99% of the time, you lose money, just to what extent.