Looking for gear recommendations — am I overthinking this?

Quick context: I am relatively new to this and trying to find my footing.

I tried three different approaches and none of them felt quite right. Been thinking about this for a while and curious what the community thinks. Mostly thinking out loud — feel free to push back hard.

Mostly thinking out loud — feel free to push back hard. I want to write something more comprehensive about this later but starting with a quick post to gather thoughts.