i can speak to Chevy but i can for ford (4 owned - 300 i6, 4/5 speed) and dodge (1 owned 318 / auto). all my trucks have had tranny coolers which makes a HUGE difference for towing by taking some heat off from added strain.
the fords i have run 1000-2200 in bed with a 4500 pound tandem trailer with between 1000-7500 pounds in load.
the dodge has regularly seen 800-1600 in the bed with a tandem trailer about 2000-4500 lbs and loads between 1500-8000.
load your bed first after hooking up trailer. load the trailer next and shift weight to keep it over trailer wheels and towards the back more off the tongue and rear axle. with practice you can really pack in weight and not worry about damage.
having a well designed trailer helps immensely to distribute weight and increase load.
as for what it can pull every one is different. i pulled 3500 pounds regularly with a 305 th200 auto tranny on my 84 Pontiac Parisian ( Chevy caprice ) in the form of a trailer and toys or a boat. just used truck tires on the car to get more bite and weight capacity. so you should be fine at the very least with 1500-2000 pounds on trailer.
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