Overrated pricing changes vs the alternatives [v3]

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. Spent the last few weekends digging into this and the deeper I go the more questions I have.

For context, I am working with a pretty modest budget so high-end suggestions probably will not land.

Not sure if this is the right place to ask, mods please remove if it is not. This came up at a meetup recently and the room was split, so curious what the broader community thinks. Mostly thinking out loud — feel free to push back hard.