Another common issue is that it is hard to see very clean oil on a dipstick.
I would be more wary of overfilling than underfilling.
What I usually do on marine engines is to fit the filter, which is usually horizontal. Then I fill to about half way up the dipstick, then hold the stop control in and spin over on the starter until the oil light goes out. This means the filter is full.
Then I leave it a while, and check again, then refill to about the half way mark, and restart the engine, and run for a while to check for leaks on the filter. There is no drain plug, they have a built in pump to empty the sump.
Then I leave it overnight, and check it again. I like to leave it about half way up the dipstick, so that on later checks I know if the oil is rising or falling, both of which indicate trouble.
I never measure the oil, maybe a quick glance at the marks on the container to give a rough idea. Measuring is a bit of a waste of time. You never get the whole amount out, and when filling, some oil will also be smeared up the side of the container, inside funnels, and so on.