RBOLTEN -
I just got thru with similar problem. My '99 put 5-6 qts. of oil into, and thru, the radiator and overflow bottle on a trip from Houston to Vidor (100 mi. )
The oil cooler referred to is located inside the block and is accessed by removing the oil filter mount. Be aware that there are two gaskets required to R&R the oil cooler. When I removed it and pressure checked it, no leaks were to be found there.
Then it was OFF WITH THE HEAD.
What I found was a deteriorated area of the fibrous headgasket material between cylinders 3 & 4. This was not very easy to see, but after studying every possible avenue where oil could get to the coolant, this came to light.
The oil (under more pressure than the coolant) was being forced from the oil passage, to a headbolt hole, and then to a water jacket passage.
After milling the head for flat and having the valves cleaned-up, I reassembled everything and am once again happily pounding the pavement.
One thing to watch with the headgasket - I strongly suggest going to Cummins to get the parts. I started at a Chrysler Dealer and got more grief than anything else. For some reason, and after contacting the regional parts rep, the ONLY headgasket that Chrysler could come up with for my engine DID NOT FIT! Funny thing is - everything I got from Chrysler was in a Cummins box.
I ended up calling Cummins Southern Plains in Houston 713-679-2220. If you look at the gasket very carefully, there is a seven digit number embossed in one surface. With either that number, or the engine serial number found on a plate on the side of the injection pump mount @ the driver-side front corner of the engine, the correct Cummins part can be had. In my case, the original number had been superceded to a new number. The Chrysler regional parts rep didn't have a clue why they coldn't get the right gasket.
This may not be your problem, but hope it helps you out.