please feel free to correct me on any of this. is it possible for a high energy free electron to collide with a low energy photon? If so, what happens? And can this be replicated in a laboratory setting?
Consider an electron at rest and a high energy photon colliding. It's the same process as the one you described, though viewed from two different reference frames. So, yes, it can happen. Nothing out of the ordinary happens. Your last question depends on whether you want the experiment done in a particular frame.
In Compton scattering, the electron recoils, and the photon back-scatters. Each time the Lorentz frame changes from/to the lab frame to/from the electron rest frame, the photon gains energy by factor 2γ.