Looking for common pitfalls — what would you do? [v3]

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. Long-time lurker, first-time poster.

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

This came up at a meetup recently and the room was split, so curious what the broader community thinks. I tried three different approaches and none of them felt quite right. Looking for honest feedback, not validation.