My 94 E320 has stripped oil plug threads in the oil pan, such that I can't tighten the plug properly, resulting in an oil leak.
First I tried to re-tap a bigger thread and use a bigger plug but it didn't work out as expected: the new thread came out slanted in relation to the sealing surface on the pan and the oil leaks continued.
Next step I decided to go all the way and change the oil pan.
I followed all the good practices for the job and now I have the engine lifted as far as it can go, the oil pan is loose, but there is no way the damn oil pan will come out.
I heard that putting cylinders 5 and 6 in top dead center will help clear the pan out.
Anyone has experience with this type of issue? Please help!

Is the pan hitting the oil pump pickup? If yes, can it be unbolted and dropped into the pan?

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"Rudeness is a weak man's imitation of strength" - Eric Hoffer

I really don't know, but I will check that, thank you!
One thing I just realized is that I did not remove the oil dipstick and pipe and they could be interfering.

Sway bar out of the way?

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"Rudeness is a weak man's imitation of strength" - Eric Hoffer

Yes.

https://www.pelicanparts.com/techarticles/Mercedes-W124/59-ENGINE-Oil_Pan_Gasket_Replacement/59-ENGINE-Oil_Pan_Gasket_Replacement.htm

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"Rudeness is a weak man's imitation of strength" - Eric Hoffer

Thanks for the link. I did use it for the job.

Finally I was able to remove the pan. To get it out I had to remove the oil dipstick tube and the drag link with steering damper.

Have to do with my 300SE, similar ordeal. Not looking forward to it.

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1979 Black on Black, 300CD (sold), 1990 Black 300SE, Silver 1989 Volvo 780, 1988 300CE (vanished by the hands of a girlfriend), 1992 300CE (Rescue).

Jorn, IIRC you had an M103 that was sludged? Is this the one?

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"Rudeness is a weak man's imitation of strength" - Eric Hoffer

No sludge in my 300SE, it's my daily driver and runs butter smooth.

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1979 Black on Black, 300CD (sold), 1990 Black 300SE, Silver 1989 Volvo 780, 1988 300CE (vanished by the hands of a girlfriend), 1992 300CE (Rescue).

Sorry, my mistake, I was thinking of someone that revived a very sludged M103 and was wondering if it survived. It looked like FlexSeal under the valve cover.

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"Rudeness is a weak man's imitation of strength" - Eric Hoffer