I'm signing this project off as finished as I don't intend on doing another board revision, the second revision accomplishes the design goals. The remaining work I intend on doing is writing up about points of interest, and ensuring the BOM and CAD files are up to date.
Here are a couple of close-ups of the second revision:
I used exposed copper on the bottom to replicate the pocket operator visuals.
Two versions of the hardware exist: one with burst mode enabled and the other using traditional pulse skipping. R4 enables pulse skipping, R5 enables burst mode (stuffing both leads to a damaged USB port).