Ok got a mechanical gauge on it, and the mystery only deepens.
Background info - The mechanical gauge setup I used uses a pass-through block that screws on in place of the oil filter, and has a port for a mechanical gauge fitting. So during testing, the oil filter was not installed.
Before the install, I went out to the driveway, started the truck, gave it a few seconds to get the oil flowing and warm up a bit, and the erratic behavior began almost immediately. Cluster gauge all over the place. Pulled the truck in the garage, shut it down. Installed gauge contraption and routed gauge up to the side of the truck so I could hold it with my left hand and steer with my right. Started truck, backed out of garage and through driveway, all readings normal (PSI 40ish on both gauges). Tried moving up and down the driveway a few times (this was more than enough to get it to act up before) and readings stayed right around 40 the whole time. Backed out of driveway and did a loop around the neighborhood, again, no weird behavior. Pressure lightly fluctuated between 35-50 psi, both gauges in lock-step. In all I drove around for about 15 minutes and never saw a single hint of erratic behavior, and both gauges agreed the whole time.
So the oil filter would then seem to be the culprit. I re-installed it and the erratic behavior did indeed return (going by only the cluster gauge of course). Open and shut case right? Except this is the second oil filter i've tried.
Since it's cheap, i'm heading out to Autozone to get a Mobil 1 or Bosch filter. I don't have a lot of confidence in anything at this point but another $15 is well worth the try.