Should workflow tweaks [v4]

The trade-offs here are not obvious to me and I keep flip-flopping. Been thinking about this for a while and curious what the community thinks.

Long-time lurker, first-time poster. Mostly thinking out loud — feel free to push back hard. Looking for honest feedback, not validation.

Long-time lurker, first-time poster. Mostly thinking out loud — feel free to push back hard. Quick context: I am relatively new to this and trying to find my footing.