Recommendations for pricing changes after a year [v3]

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.

Posting this here because the relevant subreddit has gotten too noisy lately. The trade-offs here are not obvious to me and I keep flip-flopping. Spent the last few weekends digging into this and the deeper I go the more questions I have.