Is long-term planning vs the alternatives [v3]

Quick context: I am relatively new to this and trying to find my footing.

Looking for honest feedback, not validation. This came up at a meetup recently and the room was split, so curious what the broader community thinks. Looking for honest feedback, not validation.

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.