That's interesting. On one of our previous boats, when you first pulled out the dipstick, it didn't show any oil on it until you put it back in and pulled it out a second time. It took me a little while to figure out was was happening. The dipstick was sealed well enough at the top, that the sealed tube wouldn't allow the oil level to travel back up the tube after running it until you vented it by pulling out the stick. Could that be part of your issue? Or maybe the stick is bent a certain way, so depending on which way you stick it in, it deflects to the high side or the low side.
Otherwise to know for sure, add the required amount of oil to the motor after and oil change and see where it hits the stick.
1983 Fraser 41
La Conner, WA
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Boating for over 25 years, some of them successfully.