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After all of that, I was ready for the first trip up the winter road in mid-December 2015. I'll be doing a full write up on the trip in another thread, but suffice it to say it was quite the trip.
On the way back from the +3000km round-trip, I noticed an oil leak and my oil level was really low. With no place to stop for repairs before home, I filled the oil and made sure to check it frequently until we got back home to the city.
When I got back, I saw more oil leaking around the #1&2 cylinders and the intake from the turbo.
Well I took it to the shop and we searched some more and found oil leaking on the back of the engine - all signs pointing to a blown head gasket. They pulled the head and found out, not only why there was an oil leak, but also why the #4 cylinder had low compression. Turns out at some point in time a glow plug or something must have broken off and fallen in the cylinder because it was scored and pitted and the head surface was slightly warped and pitted as well.