As someone that's lived his life 1/4 mile at a time, supercharging and turbocharging my sporty cars for fun.
For the 5.7L, IMO it doesn't really lack power for even the heaviest rated tows. It's more about preserving drivability with mods. By that I mean having the right gearing to access the powerband. As a gasser, that powerband is at revs higher than some are comfortable revving to, but with the right driving style, it's got solid skookum and gearing stock. As we modify, particular with larger tires, that can affect drivability.
Forced induction and midrange HP can help to your point, but the concern is that it's creating more combustion pressure, heat, and stress. Both to the engine and transmission. Towing is the long game and reliability and efficiency is the name of the game.
The 8 speed with the 3.31's just can't access the higher revs sometimes. Thats the problem. That power well we were talking about had me at ~3500 rpm at 55 mph. It would not drop another gear.
As you said, you can force by creating more torque, or you change the gears to give you more revs in the same gear or possibly be able to access a lower gear you couldnt before.
My one justification for a blower maybe not being a big deal is that I am at 6500'. If the blower only makes 6 psi(1.41 pressure ratio)at sea level, then that would only put me a 1.8 psi of boost here. I'd barely be making more power than a stock LX at sea level. I also wonder if making a tune that sets the shift points to shift so that you dont get access to the full power of the blower while towing.
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