Overrated long-term planning — am I overthinking this? [v5]

The trade-offs here are not obvious to me and I keep flip-flopping. There is a lot of conflicting advice online and most of it is from 2019.

This came up at a meetup recently and the room was split, so curious what the broader community thinks. For context, I am working with a pretty modest budget so high-end suggestions probably will not land. There is a lot of conflicting advice online and most of it is from 2019.