Recommendations for pricing changes — am I overthinking this? [v2]

Spent the last few weekends digging into this and the deeper I go the more questions I have. Quick context: I am relatively new to this and trying to find my footing.

Quick context: I am relatively new to this and trying to find my footing. 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.