Looking for pricing changes on a tight budget [v4]

Been thinking about this for a while and curious what the community thinks. Spent the last few weekends digging into this and the deeper I go the more questions I have. Been thinking about this for a while and curious what the community thinks.

Mostly thinking out loud — feel free to push back hard.

Long-time lurker, first-time poster. Not sure if this is the right place to ask, mods please remove if it is not. Maybe an unpopular opinion but here we go.