Show & tell: long-term planning — am I overthinking this?

Maybe an unpopular opinion but here we go.

This came up at a meetup recently and the room was split, so curious what the broader community thinks. I want to write something more comprehensive about this later but starting with a quick post to gather thoughts. Maybe an unpopular opinion but here we go.

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