A couple of reviews I saw on the subject. You likely won't be happy towing that large of a rig with the 1500.
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Hauling and Towing
When properly equipped, the Silverado 1500 can tow up to 12,000 pounds and haul up to 2,108 pounds, which is good for the class. Reviewers say the V6-powered Silverado has plenty of power for towing 5,500-pound trailers. Some reviewers say the 5.3-liter V8-powered Silverado could use a bit more power and a firmer suspension after towing a 9,000-pound trailer. As a result, they say anyone needing to tow closer to the max tow rating may be better served by a heavy-duty pickup truck. One reviewer says that the six-speed transmission is not geared optimally for trailering, and notes that power lags at times. With a half ton of cargo in the bed, reviewers say that the rear of the truck squats minimally.
"We got to drive Silverados with 1,000-pound boxes in the bed, which gave us the opportunity to see how the chassis dealt with heavier payloads. Although we would have liked some kind of load-leveling capability, the visual ‘squat’ to the trucks was minimal and the handling and rear-end control on our drive routes were well within our comfort zones." -- PickupTrucks.com
"The 4.3-liter generates 285 hp and 305 lb-ft of torque. While towing a 5500-pound camper using a trailer hitch, the Silverado never hesitated. It accelerated quickly and the integrated trailer sway controls, which use the truck's anti-lock brakes, helped steady the trailer down the windy Texan roads." -- Motor Trend
"Later, we towed a skid steer on a flatbed that checked in around 9000 pounds, and only then did the 5.3 feel a bit overmatched and the suspension a little too soft. Yes, the Silverado can handle a load this heavy (some Silverados will be rated to tow 11,500 pounds) but it felt like a job better suited to a heavy-duty pickup." -- Popular Mechanics
"But despite the pull of the Silverado's huskier new engines, we've noticed that there's still too big a gap between the transmission's gear ratios when towing." -- Edmunds
[COLOR=]2003 Keystone Challenger 31RLB 5th Wheel
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TORKLIFT StableLoad
Everyone is entitled to my opinion.