I don't know if my opinion will be helpful, but I'll share in the hopes that you get some idea of how I personally deal with these choices. Perhaps as more of us talk, you'll find a system that works for you.
The most important thing to remember is that it is a personal journey and there's no right or wrong way to edit, only the way that brings you personal peace.
In relation to the points I've quoted:
1/2- For bags I don't use frequently, I ask myself if they serve a specific function that can justify keeping them. For eg- my beater bag for when I'm volunteering (anything else would be inappropriate in a shelter), no-brand bag for when I'm travelling, the one bag I can rely on when it's pouring down rain. Bags like those are not used regularly but they are necessary in my life because my other bags cannot serve these very specific functions. They get kept in spite of infrequent use.
The remainder are the ones I downsize from. If the bag size is not functional for my life, if it is too heavy, if I don't feel like it's my style, then I do not try to make it work no matter how much I like the way it looks. I just release it knowing that someone else will love it and it will be perfect for them.
Bags are meant to be functional and to tote your stuff around. We get caught up in the beauty of them but, at their core, their purpose is to function. If they do not function for you, let them go to someone who can make them work and trust that you've uplifted someone else and improved their situation with your generosity. This will bring you more joy than looking at that bag on your shelf and feeling frustrated or guilty that you're not utilizing it.
I've said this somewhere up thread, we can appreciate beautiful things without needing to own them. And we can be grateful to have owned them for a season of our lives without needing to carry them into the next season.
Having said all that, with regards to your
Gucci satchel, is it possible to have it reworked into something else? I know a friend of mine once had a cobbler turn her tote bag (that had been damaged in one section) into a pair of shoes. He used the bag's printed leather as the front/ top of the mules, and used his own materials for the rest of the shoes. And he even made her a key chain from the remaining scraps of leather.
If there's a way to repurpose it, then that would be ideal. Or else, let it be the one display item that you enjoy as a piece of art. Having a single bag like that is not an issue in my mind. It's when you have a plethora of them that it becomes a weighty load.
3- I have had to move a lot in my life and I have let go of a lot of expensive things in my time due to those moves. Letting go of sentimental and/or expensive items is hard, particularly when you adore those items. But I personally have made it easier on myself by reminding myself of this:
The money is already spent. Having an item that
represents that money in my space doesn't bring the money back.
So, if you can recoup even a bit of your loss from consignment/ reselling directly, please do that. Some money in your account is better than nothing. It's not a loss then, it's a gain (however partial, it is still actual money).
If that's not a viable option, then it's still okay to gift your bags and consider the money lost a charitable donation of sorts, because that money is long gone anyway and that bag unused on the shelf isn't bringing it back.
Sometimes we spend our money incorrectly. That happens to
everyone. It's okay. More money can always be earned, and the peace of mind of letting go of dead weight is far more valuable than the $ amount you spent on that item to begin with.
4- Goodwill may not be a good option, but there are other ways to donate. For instance, I gifted several bags to coworkers who admired them. My mother has gifted her things to her nurses and even janitorial staff in various hospitals and clinics she has worked in. Those people would not have been able to purchase items of that quality in their financial position, so they really appreciated the bags and used them with joy (obviously I'm not suggesting you gift an Hermes or Chanel as that would make the recipient uncomfortable, but you could do this for lesser known/ no-name bags that you don't love because the recipients likely will adore them). Another user on tpf whom I PM with has done exactly the same with her unwanted bags this past year.
If coworkers and friends aren't an option, I always like to donate to places like Dress for Success. Or if you know someone whose kids are just graduating university and will be starting their job hunting, gift their kids a suitable bag for interviews. Giving someone a professional leg-up is one of the greatest gifts you can give.
The flip side of this coin- I gave my friend's grandmother one of my most expensive bags that I had only used twice. I noticed her looking at it when I was visiting, and on her 90th birthday a couple of months later, I had cleaned and conditioned the bag, put it the original packaging and gifted it to her.
She had never owned a really nice bag in her own life, and I explained to her that I picked it up for myself and used it twice, but would be much happier and truly honoured if she would accept it as a gesture of my love for her. She lived to be 93 and used my bag everyday in those 3 years- mind you, she rarely went out at that stage, but she sat it beside her when she had visitors and used it when she did go out. She was overjoyed with owning it and, I hope, touched that I gave her something I loved. I never regretted letting go of that bag, in spite of how much I had initially longed to own it, it went to a much more deserving person. It's one of the happiest memories I have.
My point being that there are different avenues for donations that we may not even realize because we're used to donating to specific charity shops.
This post is much longer than intended- as so many of mine end up being. Sorry! I hope it helps a little. I'll just reiterate that the process of editing is a personal journey, so please note that this has been my approach but it may not resonate with other people.