Has anyone tried pricing changes on a tight budget [v4]

Quick context: I am relatively new to this and trying to find my footing. I want to write something more comprehensive about this later but starting with a quick post to gather thoughts. The trade-offs here are not obvious to me and I keep flip-flopping.

Long-time lurker, first-time poster. Been thinking about this for a while and curious what the community thinks. I tried three different approaches and none of them felt quite right.