Everything has about been covered. Something easy to check, be sure the oil is not contaminated with gas. That can happen gradually if running rich, or it can flood the engine if the fuel valve is left on when stored.
Like said, those don't need much oil pressure. Being a flat head, there is no need for high pressure, no rocker arms to oil.
If you can get any pressure at all at warm idle, and the pressure will come up to 10-15 revved up, and there are no new noises, like deep knocking under load or rattles when coasting down, it will go a long time.
Gradual pressure loss is normal for a well worn engine. But sudden loss, or total loss, or fluctuating pressure, is a sign that something has changed.
One thing that will not increase idle pressure is stretching, shimming, or putting a stronger spring in the relief valve. As long as the relief valve is seating fully, it only effects high speed oil pressure.
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Today's Featured Article - Earthmaster Project Progress Just a little update on my Earthmaster......it's back from the dead! I pulled the head, and soaked the stuck valves with mystery oil overnight, re-installed the head, and bingo, the compression returned. But alas, my carb foiled me again, it would fire a second then flood out. After numerous dead ends for a replacement carb, I went to work fixing mine.I soldered new floats on the float arm, they came from an old motorcycle carb, replaced the packing on the throttle shaft with o-rings, cut new ga
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