I beat the piss out of my 00 Tahoe (older body style) 5.7 V8. So I can't complain. The only thing I have done is replace the upper ball joint, fan belt, rotors/pads, and the fuel filter. I have no idea why the ball joint failed unless J-turns/bootlegger turns are hard on 'em.
The barkes on the older Tahoes are terribly undersized. If I was lucky I could get a few thousand miles out of a set of pads. I warped 4 sets of rotors and the last set I put on were slotted Brembos. On a positive note, I get a relaxing full body massage everytime I hit the brakes. Only real issue is if I try to shut it down at speed I have to re-adjust the mirrors.

My trailer has brakes....
I had an S-10 Blazer that I put a V8 in and one day while towing a K-5 back from Buena Vista, I pulled off the road to let some cars pass and almost ended up in a ball. The whole setup jack knifed and push me right to the edge of a pretty steep dropoff. I thought a Tahoe would be big enough but it seems to get pushed around at times.
My truck has developed a vibration now that does not go away and the tires have been rotated and balanced. The people that have had tranny problems said this is the warning sign it is about to go.
I agree that the duellys are probably too much. I'll look into the 2500 as long as I can get the diesel.