A class added a method with a require or dynamic definition and that was cause to crash a production activity of some kind? You'd discover the attempted modification via a new FrozenError being raised unexpectedly and crashing what you were doing.
Ruby is made to let you extend core classes--Rails does it all over the place. If I put a require behind a feature flag, this is probably going to surprise me when it fails. It might also make junior devs think gems "don't work" or are buggy if you use it in development, when they work fine? How well does this play with dynamic class loading in dev work in Rails? I would think it would be problematic as you can't draw a line in the sand about when everything is loaded, so it is a safe time to "freeze."