The question is not rather the H2 will do it or not.
A 6 liter vortec will pull the ass out of a cat. As for braking? 4 wheel disk under 6000lb H2 will stop a freight train. Not to mention your trailer will have it's own brakes.
The issue is doing it on a regular basis. The tranny in the H2 is undersized. It's essentially a beefed up version of what my buddy has in his compact chevy blazer.
Would a aftermarket tranny cooler help? Of course. But from what I've read you can expect a 20 degree drop in temp. Is that enough to eliminate the problem? I doubt it.
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