Help me decide between late-night thoughts — am I overthinking this? [v1]

Spent the last few weekends digging into this and the deeper I go the more questions I have. There is a lot of conflicting advice online and most of it is from 2019.

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

Been thinking about this for a while and curious what the community thinks. Mostly thinking out loud — feel free to push back hard. The trade-offs here are not obvious to me and I keep flip-flopping.