Show & tell: gear recommendations — am I overthinking this? [v4]

I want to write something more comprehensive about this later but starting with a quick post to gather thoughts. I tried three different approaches and none of them felt quite right. I want to write something more comprehensive about this later but starting with a quick post to gather thoughts.

Maybe an unpopular opinion but here we go. Mostly thinking out loud — feel free to push back hard. There is a lot of conflicting advice online and most of it is from 2019.

Spent the last few weekends digging into this and the deeper I go the more questions I have.