For example, I currently have 2 different membership plans that customers can select from (e.g. Silver, Platinum). In addition to the product pricing being cheaper for "Platinum" members due to these members paying a monthly fee there are also other services I offer at this level that the "Silver" members don't receive. So my question is, should I just "simplify" the product pricing and make it the same for both membership plans and entice users to join my "Platinum" plan based on the other services I would offer at this level?
Your question really boils down to one fundamental question: are there different segments?
Undoubtedly the answer is yes. I have never seen a business that doesn't have different segments.
So what you are really asking is have you done your segmentation properly?