OK, so I got the drain re-done. Had to remove the intercooler, remove the old drain line (which had a bunch of oil in it), remove the thread-to-barb nipple, and installed a thread x thread 3/8" elbow. Not much room to work, but got it in there. Clamped on some clear line so I can see what it's doing (draining, filling, etc.). Going to take it for a test drive in the morning to see if it smokes at all or if it cured the problem.

I did start it up just to see what it would do, and it drained fine. The last picture is with the truck running and the oil draining. Not sure how long it will stay clear, but I like being able to see if it's draining or not.