Thank you guys so much for your guidance.
I have no idea who rebuilt my engine - many years ago - but I'm now a little worried there might be other misassembled parts. It makes complete sense how you've described the rocker shaft oiling should work. What I'm seeing is a steady stream of oil out the back rocker because the holes in the shaft and rocker are completely lined up and the oil can flow freely out the hole. Unfortunately it will be a while before I have time to do this because of traveling, but it will definitely be at the top of my truck work items. I will also try to straighten that push rod in my press. Worst case I have to replace it. Might as well try to fix it first.