Excellent discussion. I don't really have a good answer, just a few random thoughts:
I've spent much of my adult life accumulating things. Now I feel like it's a weight, and I'm shedding stuff at a slow but steady pace, as time allows. It's not about money, I have little debt and have a good job and could easily buy more.
The rifle collection has been mostly pared, it's the handguns that are still too prolific and I'm struggling with deciding what to get rid of. That's ironic, because none of the ones sold in the past have been missed. I feel like if all those guns weren't in my safe it wouldn't be hard to get by with replacing just a couple. I have at least stopped buying more.
That said, there are a few guns I'm keeping simply because I enjoy them. I don't "need" them, they're simply fun to shoot.
There are days that I envy the fictional Jack Reacher, wandering around with just a toothbrush, a debit card, a passport, and a few dollars cash. I couldn't do it without hurting those close to me and I'm way too responsible anyway. Still, there's the fantasy and curiously, a couple of close friends have told me similar stories.