Weekly discussion: late-night thoughts — am I overthinking this? [v1]

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. 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.

Been thinking about this for a while and curious what the community thinks. There is a lot of conflicting advice online and most of it is from 2019.