Why pricing changes — what would you do? [v2]

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. Maybe an unpopular opinion but here we go.

Quick context: I am relatively new to this and trying to find my footing. For context, I am working with a pretty modest budget so high-end suggestions probably will not land. Looking for honest feedback, not validation.