Weekly discussion: long-term planning vs the alternatives [v3]

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. I want to write something more comprehensive about this later but starting with a quick post to gather thoughts.

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