Thanks for all the suggestions. I did check the tire pressure on the trailer as well as the lug nuts. As for the truck, I did not check the pressure and they are the same stock tires the truck came with.
I also checked the set screw that snugs up the head tilt. But I did not check the Nuts and bolts. I will put that on my list of things to check.
As for the lift, i usually lift the rear of the truck about 3-4" prior to put on the bars. I didn't notice if the bars were any easier or harder to install. I do know, since the hitch was new, that one bar is always more difficult to snap in than the other.
When hitching up for this trip I was running late and maybe did not lift the truck enough. I will have to keep that in mind when I check everything out this weekend.