I struggle with discord too and mostly stay out of the large group chats these days.

>One thing that has never resonated with me is sentimentality. I just don't get it. I'm too pragmatic, I think.

I don't collect things, I let them go. But, I do apply meaning to memories of things, moments shared. For example, I remember places I have visited through the photographs I take - not the actual photographs - my process of taking them. There is far more information I hold in that process than the result. So, the value of the photograph carries with it my sentiments of the moment I took it and when I see/remember the photo, I can transport myself to the moment I took it and *why* i took it. 

>Meaning to me comes from my analysis and comprehension of patterns and teachings from life, life lessons.

Which I think is what this encapsulates. The thing itself is valueless, but the patterns and lessons it brings to mind might be priceless. While you might hold that value through the process you have gone through, another holds the process in the thing that works as a trigger for the memory. Maybe it has to do with the type of memory people have?