Yeah. I've been completely unable to find the leak, it's like it's not leaking anymore. I need to get the entire bottom side of the car cleaned to better find the leak. I'm wondering if it's coming from the engine block? I kept the air filter off, left it running for 10 mins, revving it and everything while looking around the engine bay and underneath. The only drip I saw came from the exhaust pipe from the middle of the car, probably because I didn't clean that at all. Kept the air filter off and that entire side of the engine stayed dry. Though I noticed a small bit of wetness on top of the exhaust pipe.

if the pcv hose gets pinched these engines have been known to puke out a lot of oil. Is it possible the pcv hose got pinched off.

Now that sounds like it makes sense

The oil flow to the cooler is thermostatically controlled. So, if the leak was there, it might not leak with a cold engine.

Yes. But how would that account for oil on top of the exhaust manifold?

I'm going to bet the crankcase vent hose is plugged, or pinched, the air cleaner popped off it's drain, and pressure built up and the checkvalve is stuck open letting the oil pan puke it's guts out...
I see no oil on the pressure side of the turbo, so it didn't come from the cooler and get sprayed by the fan... the exhaust side of the turbo is covered in oil... I think it's got to have come from either the turbo feed line or dumped out one of the return lines on that side of the motor...

Good suggestion.

It could be one of those extremely rare MB diesel engines with more than one oil leak. Hard to envision, I know.

I am about 70 miles north of Columbia.

Sounds like a winner. What is recommended now? I'm gonna get a new vent hose because mine had a tear in it, and it was crap. I'm getting a check valve too. For that job, what else is recommended to do while I'm in the area?

Awesome silber, I go to Kirksville

I read through this guide, PeachPartsWiki: Replacing the Oil Separator Check Valve and have the part number for the check valve. Does anyone know the part number for the holding sleeve? I can't seem to find it.

At this point you still seem to be shooting in the dark. If the vent hose had a tear in it, that counts against the hypothesis that a pinched vent hose caused your problem since gases could escape from the tear. Personally, I wouldn't do anything until I had a better idea of where the oil leak was/is. I'd wash the engine down completely, get the engine up to a very warm temperature and look closely for leaks before taking further action. Qwerty's hypothesis has yet to be tested.

Well I still have more to look at, but it seems the best so far. the tear was in the crease and it's only open when you pull it up out of the way. My air filter is missing a bracket, and sits too low so it has been pulling the hose down and closing off the tear by pinching the hose. And now that I've thought about it, since I was extra special about making sure the air filter sat on the drain tube, I ended up making it sit even more lower and lopsided. It previously had a rag under it holding it up. So I'm trying to find one of those brackets. The oil separator needs to be replaced regardless because it put a lot of oil inside the air filter housing... So I'm gonna do that but I wanna get as much done as I can at the same time.

The only oil entering the crankcase ventilation circuit would be in vapor form. There is no reasonable way that a leak in the vent system could be responsible for significant oil loss.