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My experience is limited somewhat, but I remember skiing behind my dad's boat (an "off-brand" tri-hull with a deep center v) back in the lat 1970's/1980s. That boat was an 18', standard construction walk-through with a 115HP Johnson, 2-stroke. That motor would jump that boat up real quick, as most describe for 2-strokes. For a young skier, that boat would yank the tow rope right out of my hands from time to time.

My present boat is a 150 Super Sport (the recent model) with a 60hp 4-stroke. There IS a bit of squishiness at first start with this motor, but I'm imagining being on the end of the tow rope and having a much nicer pull up and out of the water. I haven't skied behind her yet. But this squishiness is the first couple seconds, and after that, she's all powerful and mighty. Plus, she doesn't stink (though I grew to associate 2-stroke exhaust with boats, outdoors, fishing, fun, and sex). And, she RUNS whenever, wherever, every time, especially good down in the low-RPMs.

I guess my point is ... one big, tough 4-stroke motor is going to bring more overall pleasure for more overall purposes than any other solution. The only exception I might make is if you had two smaller motors with completely separate fuel systems and you're going to places where you absolutely, positively are beyond towing. And in a 21' Outrage ... that's probably not going to ever happen.