Daily thread: common pitfalls — am I overthinking this?

The trade-offs here are not obvious to me and I keep flip-flopping. Posting this here because the relevant subreddit has gotten too noisy lately.

Been thinking about this for a while and curious what the community thinks. Looking for honest feedback, not validation. Long-time lurker, first-time poster.

Posting this here because the relevant subreddit has gotten too noisy lately. Spent the last few weekends digging into this and the deeper I go the more questions I have. Maybe an unpopular opinion but here we go.