Hey guys, what do you think about the attached pic?

This is an '82 240D 616 with 249,600 miles. You're seeing the front driver's side of the block from the top down, looking down on a huge bolt head whose recess is constantly filled with oil.
I have had a pretty considerable oil leak coming from high up on that side of the block but it only leaks under higher loads, like 65mph highway driving. I cannot see any leak if just at idle, but if I park after cruising the highway I always drip 4-6 drops onto wherever I park.
This is NOT the valve cover gasket. I replace that after every valve adjustment without question. All clean on the side of the head. Difficult to diagnose any other potential gasket leak since I'm unable to watch it happen. I can sop up the oil from the bolt recess and it'll be full after the next time I pull in from such a drive.

So it occurs to me that the next seal above this bolt recess that might blow oil under load is the head gasket. I have no other signs of an internal head gasket leak, so my question is: Has anyone ever seen one of these cast-iron heads leak oil outwardly from behind the timing chain area?
I hate to do a head gasket just to get in and find out it was not torn at all, and I'm kinda hesitant to think a cast-iron head on a cast-iron block would tend to rip one. Still, it's 26 years and 250k... And then again I've never heard of a head gasket leaking "out" rather than "in" - to the cylinders.

Please let me know if any of you have any thoughts on likelihood of the head gasket, paired with seeing oil pool up around that bolt recess being caused by any other gasket.

Thanks so much!
Garrison

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Garrison R.
'83 300D