T-Bone:
The oil degrades the rubber and makes it sticky then faulty (or vacuum that can't overcome the oil and goo). The oil got into the vacuum lines because of the ck. valve failure, albeit perhaps intermittant failure.
When the truck is turned off, no more vacuum is produced (its pulling a vacuum towards the vacuum pump from all vac. components). If the ck. ball/valve doesn't hold we have things going both ways rather than one way as it should. As the acuator for example loses "prime" without the ck. valve working properly it "wicks" engine oil into the vacuum lines. I think its a gradual process over time and many cycles before it eventually migrates into the dash vac. components. Gravity also takes affect as the ones lower in the blower box are most affected typically.
You discovered the dirty side of the vacuum with oil, the oil is necessary as a lubricant for the vacuum pump. Everything is fine, unless the ck. valves failes even at times and contaminates the vac. sys. with oil.
You can cut the large rubber line leaving the ck. valve at the vaccuum pump and add an additional inline one way ck. valve that will fit your tubing. I would source the valve before cutting the tubing. I also sometimes add a second ck. valve to the line just before it enters the cab near the a/c dryer (accumalator).
I think I gave the the Mopar and Cummins part no for a new oem ck. valve. I would disassy the one you have and replace the "guts" with the internal parts from the new one from the Cummins part no (most reasonable) or simply replace the unit with the Mopar part no for complete parts change with minimal hassle.
I think the plastic retainer under the sping that guides the ck. valve ball in the metal/brass bore gets cocked or crooked causing insufficent seal and incomplete closing when the engine is shut down. Likely over the course of months or years the oil built up until enough was in the system to cause failures of certain components.
I see no need to remove or disassy the vac. pump, it operates as designed from your description, save the issue with the ck. valve.
Pat yourself on the back and think of the money you save by diving in even though your hands are still cut and bruised and cold?
50 deg. ? It was colder in Dallas today!
Good luck
Andy