OK, my 1983 380SEl has been leaking oil out the left cylinder head for about five years and it has finally gotten to the point that it is leaking about 1 quart every 500 miles if I drive around tow.
The funny thing, if I drive it on a highway trip the oil leak near stops! I've ordered all the parts.
I intend on doing the timing chain (already a double chain), all the guides, head gaskets on both sides, and totally reseal the entire upper half and front of the engine.
I've already purchased three special hex key sockets to remove the cylinder head bolts.
My question is, what problems may arise in this venture? I've heard of broken head bolts and stripped head bolt holes in the block.
I'm reusing my original bolts due to the fact that the Mercedes does not use torque to yield bolts.
I'm a Ford mechanic and this is my first major repair on old Janis (the cars name).
If anyone can offer any advice I'm open to hearing.
I just want to get my baby back on the road leak free! This has been the best car I've ever had.
She has 225000 miles on her and she still looks like new although the seats are starting to show there age.

Perhaps because V8 head gasket problems are so rare.

I did mine about 2 years back on my 82, I encountered no problem with any bolts stripping out, but I had heard the same thing. I also converted mine over to double row at the same time, did the valve job on the heads as well and overhauled the transmission.

...and thats where it still sits today. Just the block and the heads on it. Someday I'll get time to finish reassembling it and put it back in the car. Too many projects...

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1980 500SE/AMG Euro
1981 500SEL Euro
1982 380SEL
1983 300TD
1983 500SEC/AMG Euro
1984 500SEC
1984 300TD Euro
1986 190E 2.3-16
1986 190E 2.3
1987 300D
1997 C36 AMG
2003 C320T 4matic

past: 1969 280SE 4.5 | 1978 240D | 1978 300D | 1981 300SD | 1981 300SD | 1982 300CD | 1983 300CD | 1983 300SD | 1983 380SEC | 1984 300D | 1984 300D | 1984 300TD | 1984 500SEL | 1984 300SD | 1985 300D | 1986 300E | 1986 560SEL | 1986 560SEL/Carat | 1987 560SEC | 1991 300D 2.5 | 2006 R350

I did not figure the bolts would be a problem. I will find out tomorrow though. Deanyel obviously does not have much experience with the 116 engines and the leaky left heads. But thanks for the input.

Nor do other people - that was the point.

Never mind the head bolts...I stripped one of the allens (the head not the threads) holding the generator assembly onto the block last night. 20 year old bolts don't like to move. Why did MB use allen heads on the alternator brackets and hex heads on the PS brscket? My chain guide pins don't like to move either...I have tried the bolt and washer method but I don't think they make a M6 bolt strong enough...may have to break down and but the $50 tool.

Good luck w/ your project. I think if you work on it as a hobby it will be fun but if you put a time limit on it and need that car running by a certain time it'll become stressful. Enjoy!