Hello @rprince - Thank you for being a member of our CircleCI community! In May of this year, we introduced advanced config-compile-time logic statements to config version 2.1. This might give you the conditional flexibility in using your when statements you are seeking.
This Discuss Post is the general announcement & description: Advanced Logic in Config
However, one of my colleagues in Support created the following Support Article which helps illustrate this and gives some example configs: https://support.circleci.com/hc/en-us/articles/360043638052-Conditional-steps-in-jobs-and-conditional-workflows
Have a look at these articles and let us know if this helps!