Recommendations for workflow tweaks — am I overthinking this? [v4]

The trade-offs here are not obvious to me and I keep flip-flopping.

The trade-offs here are not obvious to me and I keep flip-flopping.

Quick context: I am relatively new to this and trying to find my footing. Spent the last few weekends digging into this and the deeper I go the more questions I have. The trade-offs here are not obvious to me and I keep flip-flopping.