Ok, here's the update. Finally took it to a shop that was willing to mess with things and troubleshoot. Found two issues:
1) A/C system was empty. Ugh. So I definitely have a leak somewhere. I finally gave in and went with R134 because it's a whole lot cheaper to troubleshoot a leak with R134, especially knowing it's going to leak out, and it honestly feels pretty cold. They could not find the leak right away, so I'm guessing it's around the evaporator fittings inside. Plan is to run it till it's cold, then the dye should show up just fine with the light wherever it is. I'm going to drop the dash down for them to save on some shop time too and give them easier access. They're being very accommodating in that regard.
2) Even with a full charge, the clutch still randomly will not engage. It's hard to reproduce, but turn the system off and on a few times and it seems to eventually reengage. They confirmed my findings that when it's not engaged, there is no power even making it to the pressure switch. So, it's either the control switch in the cab, or they said there is a thermostat switch by the evaporator (which Jerry and I suspected was somewhere...but wiring diagram doesn't show it). The guy said he is positive it has one, and that this switch going out is not only common, but would cause the intermittent clutch issues too. They said they could drop the dash to find it and troubleshoot it, but offered to let me take it home and do that work to get to the switch if I wanted to save on the shop time. Which I did. He even went to his inventory and pulled one out to show me what I was looking for, then told me how to test the switch. Said to bring the switch back to them and they probably have one in stock that will work. Sweet.
So, that's where I stand. Cost me $91 for the troubleshooting and full recharge with dye. Seemed reasonable. And if it seems like I'm reposting this all over, I'm just trying to leave question threads with answers in case someone searches in the future