I've been thinking about this stuff recently, too. I found that;
On brand:
I find myself prefer carrying smaller brands now. Not even a famous contemporary these days. Although I always prefer my less premiere brand for my day-to-day life, I see myself navigate toward them even more these days.
On material:
I'm having a bit of the "I think I should purge all my non-leather bags" phase the other day. I used to have this thought years ago, but I knew back then that having non-leather bags will keep my closet versatile.
I'm having that thought again now, but I'm also getting older. My lifestyle also changes a bit in details. My non-leather bags are still good and I know it'd take a lot of time and money to replace them, if I want them again, and I don't want to waste that. But I prefer my leathered ones more now. It used to be half-half, with a super soft spot for canvas. The scale is tipping toward leather more. I may change my mind again, but right now, it's definitely a change I'm keeping my eyes on.
On style:
Messenger bags used to be my favorite style and I used to despise handheld, but since my shoulders hurt badly last year, I find myself prefer handheld and loving it more everyday. I put my messenger bags on lately and it's not as comfortable as it used to be. Even with the satchel, I used to prefer the straps, but now, I use strap just when I'm in a rush. I prefer to grab it by the handles and a handheld tote is becoming a favorite. I don't think I'll get rid of all of my messenger bags, but I'm definitely considering retiring some of them that are too big to be comfortable now.
On size:
I prefer my smaller bags now and won't go any bigger than my Bally Wide Horn. That's why I'm letting many bags go and finding them a new home.
On Criteria:
I used to pick bags based on style, material, then size. Now, size is number one.