Looking for workflow tweaks after a year [v5]

Long-time lurker, first-time poster. Maybe an unpopular opinion but here we go.

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.

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. Looking for honest feedback, not validation.