A/B testing. Try something like coupon codes or just two different plans that are presented as "basic plan" (or whatever. Some get plan 1A, some 1B.
Also don't underestimate the value of the more expensive plan to making your $4.95 plan look cheap. A simple answer to what could be premium is contained in your terms: Make the $99/month plan suitable for use in a production environment, as web middleware or a backend, etc by relaxing restrictions and having some sort of SLA.