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?
As you likely know, people make a lot of decisions based on price. Having different pricing points isn't distracting, it's often the driver for making a decision - as people compare value of an offering to the price of its offer. So no, I don't think you should set all your prices at the same level.
But I do suggest you put prices on them (not just free), as studies on membership sites have shown that even a $1/year price will see 15-25% of previously "free" users leave - meaning that they never had the intention of spending money with you.