Can o' worms 90 degree oil filter adapter

Bought this car 5 + years ago and drove home 120 miles +/-. This adapter always leaked but valve problems reared its ugly head before addressing leak not to mention cooling issues.

I regress to say said valve issue was
probably self infected by heavy foot.

After finding set of fresh 273 heads years later, Champion Rad, Flowcool Pump, Stewart Stat, carb rebuild etc. Still problems with possible H2O leaks and of course the oil leak at adapter.

Having given up on Mopar about '82 due to finances etc. Here I sit in quandary as WTF on adapter.

At almost 63 not looking forward to HiLift jack crawling under for initial inspection on
what I assume is factory 90 dgrer oil filter SOB. WTF Is up with bolt/plug.

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