Anyone else pricing changes on a tight budget [v3]

This came up at a meetup recently and the room was split, so curious what the broader community thinks. I tried three different approaches and none of them felt quite right.

There is a lot of conflicting advice online and most of it is from 2019. Been thinking about this for a while and curious what the community thinks. Mostly thinking out loud — feel free to push back hard.

Spent the last few weekends digging into this and the deeper I go the more questions I have. Mostly thinking out loud — feel free to push back hard.