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Y Blocks had trouble with upper oiling "back in the day". The oil gallery that feeds each valve train makes a dog leg between the block and each head, sometimes things would get sludged up. At least, it's not bone dry up there, then you know there's trouble. Additional factors were non-detergent motor oil, infrequent oil changes, leaded gasoline, short trips, out of tune, defective, missing, or wrong temperature thermostat etc.
What you might do is remove each valve train rocker assembly, and clean out the rocker tubes of sludge &c, and inspect them for scoring and galling on the underside. That's where the wear occurs. It's sort of a pressurized system of oil through the rocker tubes and around the rocker arms, and return oil then diverted to lubricate the timing chain & distributor at either end. Replacement rocker shafts aren't real expensive and probably a better idea yet. The rocker arms can get spendy.
While the rocker assemblies are removed crank the engine over with the starter and check to see that both heads have good oil flow. Modern detergent oils and fuel are much less prone to sludge. If everything gets cleaned up good and tuned up good, it will stay real clean up there.
What you are seeing was normal in the 60's because the oil wasn't all that good. Most of the engines we took apart that didn't get regular oil changes would look like that. Keep in mind there are millions of people out there that think you never have to change your oil, just add it when it's low. So if that truck sat for a lot of years it may be normal for an engine that didn't get taken care of. I'd pull the engine and drop the pan and give it a good douching. Then make sure you have good oil flow when you put it back together..
The rocker shafts are hollow, with a drilled hole for each rocker arm. If they are sludged up the wear is very rapid without lubrication getting to the rocker arms.
At the worst, loose sludge and debris could clog the oil pickup screen, causing oil pressure to drop. At the best, the filter becomes full of debris more quickly and is bypassed - the oil is unfiltered at that point but you shouldn't loose pressure.
If you took care not to drop stuff down the pushrod holes or drain holes, it should be fine. You would really have to try to knock a lot of stuff into the crankcase by cleaning the heads.
Why is the entire engine wet in the first picture?
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