Anyone towing with a '08 GM 1500?

I tow with similar truck, though a '12. It pulls our 30 foot (labeled a 27 foot but its really 30) just fine. WD set up is a must, of course, but we do fine. I would think you would be as well. As TomG2 suggests...running over the scales is a good idea.

TomG2 --- I see you are in central IL...where do you go for scales in Central IL?

Wish there was a scale around here that didn't have a line of trucks waiting. I know that would involve dropping the trailer by itself on the scale. Maybe a local quarry would let me use one

Spend $10-$12 at the local scales to determine what you have for actual weights. Most likely you will be close to or over on your payload capacity. (It takes three trips across the scale to get all the information needed to evaluate your setup)