Gonna be close.
I had a '97 K1500, 5.7/60E/3.73, on stock 265/70R17 pulling my sig trailer. Trailer was/is ~6k (give or take a couple hundred pounds). I think my trailer has a large frontal area (it is tall inside, ~7' inside at the front), so it grabs a lot of wind.
Adding an aux trans cooler IS A MUST! Your truck may or may not have the factory aux cooler (passenger side of grille). I added a B&M unit that was piped inline and mounted to the driver's side, and read transmission temperature from the pressure test port (remove plug on driver's side of transmission, located above shifter linkage).
The truck will not have a chance of OD unless headed down hill. Lock 3rd. Pay attention to when the torque converter locks in 3rd and try to keep it there. As you start up a hill and apply more throttle the TC will unlock and generate more heat.
If you plan on swapping the R&P, go with the 4.10! Peak torque was near 2500-2600rpm, which you wont achieve in 3rd unless your going faster than you should be. The 3.73 were still tall for if I was going to pull the trailer very much.
Summer time with a head wind and all I did was stare at my transmission temperature. I never took the trailer far with that truck, ended up selling and purchasing something a little more up to the task. Don't get me wrong, the power was there but the wink link is the transmission/axle gearing. If that truck would have been a 5spd manual I might still have it.
My trailer left me with a sour taste toward that truck and pulling a trailer. It just wasn't the right combination, I simply had too much trailer, and bought my trailer knowing that it was going to be close... The 6k weight on a flat bed would have been different since it wouldn't grab near as much wind.
I'm sure this muddied the water a little. Don't have high expectations of the truck, and don't expect the trans to live much longer if you do not monitor its temperature.
Oh, and of course the sales person says your half ton can pull the trailer. What they are failing to realize is the difference between towing capacities of today's half ton truck versus what they were 15 years ago!
2005 2500 Cummins/48RE/3.73, QCLB, 4wd, BigHorn, Edge Juice w/ CTS + Turbo Timer,Transgo Shift Kit ISSPro Oil and LP pressure gauges, GDP 20/2 filters, Custom Diesel Steering Box Brace
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