Weekly discussion: gear recommendations — what would you do? [v4]

Been thinking about this for a while and curious what the community thinks. Not sure if this is the right place to ask, mods please remove if it is not.

Quick context: I am relatively new to this and trying to find my footing. Mostly thinking out loud — feel free to push back hard.

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