Hey there OP! I think a lot of people have given some good insight on why people flip. It seems you have a strong perspective which is great for you but let me try again - using some already stated points and some new ones - to help you understand flipping.
I think the first thing to realize is that many of us (me included) have zero emotional attachment to their bags. They are inanimate things. When I say I "love" a bag it's really just a euphemistic way of saying it's truly beautiful to me or I like how I look when I carry it. That's it. I truly love my family, my close friends and even my silly little cat. Those are what I truly can't part with. I would hazzard a guess that many of us who wail long and loud about parting with a bag are really just enjoying the ride of engaging about purses on a purse forum. It's fun to talk about / enthuse about / dither over with like minded forum friends. But, really - it's not that deep. I think very few of us who are using funny or emotional language about getting rid of a bag really are that worried about it. In fact if you check back, many people will say they don't even think of the sold bag once it's gone and their new baby arrives. So a lot of this conversation is fun hyperbole among like minded folks because this a well enjoyed hobby.
Above you say people should give a bag a "chance" if they don't like it. I agree with you to an extent and try out my bags a couple of times before I make the final decision to punt. But, actually our opinions may not make logical sense. There may be a better bag for the person. The bag doesn't have feelings. Someone else may like the bag better. So keeping a bag past the moment you realize you don't like it can be unnecessarily limiting (and clutter producing). A bag is just a pretty sack. Why not get rid of it immediately if it doesn't spark joy?
And handbags are fashion items. Fashion. Not investments. So it's makes perfect sense to me that some very fashionable people who want to keep up with the latest fashion trends - either because it's their hobby, their career or their "thing" - will buy a bag the minute it comes out and dump it the minute it's no longer "hot". I am doing my best to buy bags I can keep forever because I just don't want the hassle of selling. But those who like to be on top of trends may need to flip to stay on the forefront of fashion. And thank god for 'em. Fashion bloggers, designers, or simply uber fashionable people in our cities and towns inspire the rest of us with the great looks they put together.
Also remember that many people on TPF aren't constrained by finances. There are very wealthy people here who can buy 20 bags a month and flip them with no impact to their financial holdings. So again, while you or Betty or Sue or I may have to consider the implications of buying a Hermes, tons of people on this forum can buy them like they are jelly beans. In that case, buying and flipping for fun is very much money "well spent". It's their hobby and they can afford it.
Others only want to spend so much on bags whether or not they can afford them. Or they have limited space in their homes. Or they simply just don't want more than x bags. In those cases it again makes perfect sense for them to think hard about their collection, get rid of bags they may love but just aren't using and sell them to fund a bag that they will love - whether or not the sold bag is a day or a decade old. And they retain their "power" to do what they want with their bags.
I'll also throw out a comment on looking askance at anyone who sells to keep up with their social circle. I'm "lucky" in that I live in the town that fashion forgot. I could wear a limited edition Hermes Berkin on my head and people wouldn't care (or know what it was other than a weird hat) So it gives me flexibility to do whatever I want. Old bag, new bag, no bag. However, everyone isn't so lucky. If you are "in" fashion you better keep up with your social circle if you want to keep your career. If you are in certain political or corporate environments (entertainment is just one) your also have to keep up with the Jones' to keep a paycheck coming. And some are simply born into certain social circles where how you look / what you carry is important for whatever reason. If they want to stay in that world, they have to conform. It's not for me to say that's silly. Why? Because all of us have some sort of currency we must pursue to "fit". In my world being well educated / smart is the currency. In Fred's, it may be the quality of his cattle. So I don't poo poo out of hand the fact that handbags could be very real part of the social currency.
So, thanks for reading my long post. I hope it helped you see that your approach of being emotionally attached to your forever bags is a very happy and rewarding place for you but not necessarily all. One of the many great things about TPF is that it's the one place that you can find many like minded people to can walk that specific journey with you. But it also has many other populations like that flip bags, horde bags, keep up with the Jones', avoid "it" bags like the plague, make profit reselling, are in debt up to their eyeballs, sell to fund, only have bags they wear to death, have huge collections they don't use, only have one bag, etc. etc. and everything in between. As I said, handbags are just pretty sacks. We'll all have very different ways of treating them.
Hope this helped you see more broadly. Enjoy your well loved bags! 😄 👍
