How late-night thoughts that nobody talks about [v2]

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

Spent the last few weekends digging into this and the deeper I go the more questions I have.

Been thinking about this for a while and curious what the community thinks.