Hot take: long-term planning (2026 edition)

Not sure if this is the right place to ask, mods please remove if it is not.

I tried three different approaches and none of them felt quite right. Long-time lurker, first-time poster. There is a lot of conflicting advice online and most of it is from 2019.

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