I'm surprised no one mentioned the three biggest deciding factors that would generally result in an increase in torque, which would thus mean greater holeshot:
Engine weight
Engine stroke
Overall engine displacement
Lighter weight is always an advantage, two strokes are generally lighter weight then 4 strokes.
Longer stroke generally = more torque. Torque is what you need to get a skiier up
"There's no replacement for displacement". You got more cubes, you generally will have the torque too. I've seen similar HP outboards vary by 10 cu/in or more!
Take for instance the Mercury Grand Marquis I drive. The outgoing Ford 5.0l that the 4.6l modular motor replaced had around 15 less hp then the 4.6 if I remember correctly. However, the 5.0 had an advantage of having a good amount more in torque then the 4.6. Horsepower in engines will not always tell you your torque, or twisting motion. If you want to get a skiier up, you need that twisting motion.
But in the real world, if all I cared about was getting skiiers up and I wanted to do it economically, I would just get the best deal on a 4 stroke and just prop it for the best hole shot (with less speed resulting, but that wouldnt matter in this situation).
I mean, if we are talking power to weight, can anything beat the stump pulling power of a Mercury inline 6 two stroke? Probably not
But can anything drink fuel faster then a tower of power? Probably not.