Help me decide between pricing changes that changed my mind [v3]

Been thinking about this for a while and curious what the community thinks. There is a lot of conflicting advice online and most of it is from 2019.

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.

Mostly thinking out loud — feel free to push back hard. The trade-offs here are not obvious to me and I keep flip-flopping. Looking for honest feedback, not validation.