What is correct orientation of dip stick handle?

I used to see that on vehicles all the time.
There's two things at play;
1) The stick goes into the oil at an angle, and
2) if the end is bent, then it will show, hi/low just as you describe,and it can vary quite a bit.
So you can't do anything about the angle deal, but you can straighten out the stick.
Or, What I do is orient the stick with the bent end trying to enter the oil as vertical as possible, and mark the handle as to which side is now up.I use a paint-marker.
Then to calibrate it, you do that at the same time as you do an oil and filter change, and after the oil has bee brought up to temp. This is the only time that you know for sure that the correct amount of oil is in the pan.
So; with the vehicle on a flat level surface,you dip it, and find the level, and mark it, and file a notch on the edge. Now you know the correct level. To make an add mark, I'll let you figure that out,lol.