Has anyone tried pricing changes — am I overthinking this? [v4]

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

There is a lot of conflicting advice online and most of it is from 2019.