Are the lifters original and/or genuine GM?
I have heard of the problem before with todays replacement lifters.
Does the bottom end of the push rod have a grove cut in it where it sits in the lifter? This is necessary to allow the air to release from the lifter. The center top of the lifter also must have a air bleed hole.
The problem is the oil gets squeezed out of the lifter after a period of time.
Also I would suggest using 5W-30 or 10W-30 as the thinner oil will refill the lifter faster when cold. Depending how "tight" the lifter is adjusted t will cause no harm, no more that adjusting a solid lifter to .020"....jst refrain from over reving the engine for the first few minutes.
The lifters and rocker arms are lubricated from the rear cam bearing and does not require high pressure, just eough to get oil around the sides of the lifters and they will automatically pump up. You could also try adding a pint of Marvel Mystery Oil to the 10W-40 oil to thin in out a little. I have used both 5W-30 and 10W-30 in my '50 with original lifters with no problem.