I’m like
@Sparkletastic in that I only want bags I will use, which means not a huge collection, but also want enough to give me some variety so I don’t get bored.
For me, there’s also the balance of form vs. function. Not every bag I own makes my heart sing, but I do LIKE them all and the ones I don’t swoon for tend to be super-functional and work well for me. I also have a couple of bags that do make me swoon that get worn very rarely, but they do get used and I love them, so they don’t get sold. It’s a rare bag that has both high functionality and the swoon factor!
The question of getting a great deal doesn’t usually apply to me since I tend to love brands that never or rarely go on sale. I’ve also tried to train myself to always ask myself if I’d still like an item if it wasn’t on sale. If I wouldn’t want it at full price, I don’t think I’ll love it on sale, after the rush of the bargain wears off.
When I do decide to sell, it’s usually because some aspect of the bag no longer works for me, or my style has outgrown it, or I’ve upgraded to a bag that is similar but somehow better, making the older one redundant. And even then, I sometimes hang on to an older bag, “Just in case.” I do fear seller's remorse, but really, between online consignment stores and Ebay, very few decisions are irrevocable. You can almost always find a bag you either missed the first time around or regret selling.
If you are considering selling a bunch of bags, I’d recommend doing it slowly. Sell one or two, pause and see how you feel. You can always decide to keep the rest of the selling doesn’t feel right.