Yea, I hate that! Fortunately my new boat has a hose on a drain plug kind of thing, but it still leaves some oil in the pan due to the angle.with the engine tilted back toward the prop, you will only get about half the old oil out through the dip tube.
I'd be scared that I might break off that tube somewhere inside the engine!I can pump virtually all my oil out by threading the suction tube down through the oil fill cap, through the push rod opening and into the very bottom of the rear sump. Took me years to find that .