What can go wrong on a "mint" 1998 E320 with 85K miles? I have a chance to buy this for around 20K. What is the life expectance of a head gasket on this car and how much to repair?

The 1998 E320 has a V-6 engine(M112) & doesn't have head gasket problems like the M104 engine did.
Only real problem with that engine is the crankshaft Damper comming apart. List price on that is $70. & takes less than 3 hrs to install.

Check the auto trans 722.6. IT does need service.

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Sounds like a good deal. I paid $23K for mine, it had 65K at the time. Check the seats. Mine go "clunk" when my body weight shifts like when going around a corner. I believe the seat frame is broken on mine, a common problem. I don't know if anyone has come up with a good repair yet.

M.B DOC, what do you mean by auto trans 722.6? Is that the type of transmission? Are you saying that the sealed transmission should be serviced by 85K miles?