As it turns out you were right! I installed the pressure plate flush and torqued it the first time I installed it, but I realized I had forgotten to align the clutch disc and it was off center. So I took it apart, aligned it and I guess I forgot to retorque the bolts when I put it back together the second time. All of the bolts were snugged just enough to flatten the lock washers, but not enough to bring it flush to the flywheel. Thankfully none of the screws fell out of the flywheel.
And to anyone wondering... the pressure plate bolts can be tightened with an open end wrench through the starter hole in the bell housing. Didn't even have to drop out the trans. Of course I wasn't able to torque it to spec with an open ended wrench, but hey tight is tight right?