Truck can pull it but what does the DOT guy with the little blue lights think? 14K trailer GVWR puts you in the CDL Class A range. What is the truck's GCWR? What is the truck's hitch rated for? Depending on your state, some are very eager to make the state some extra money.
No it does not. In most states, except CA and maybe NY, CDL range is
a GCWR of 26,001 lbs or more provided the trailer is 10,001 lbs or more.
His truck & trailer does not have a GCWR of 26,001 lbs or more. Therefore, he is not required to have a CDL.
That takes care of the licensing part. Now to the truck part:
He won't be fine until he reads his owners manual and checks his truck's TT capacity. My gues is a max of 10,000 off the bumper. I'd be he is well in excess of his trucks TT capacity IF the trailer is a fully loaded 14K trailer. O/P says trailer isn't fully loaded, but the last PA State cop I talked to said it is illegal to pull a trailer beyond your TT capacity, even if it is empty.
Your state may say differently.
You don't need to necessarily "look for a 1-ton". You need to do your homework and look for a truck that is rated to pull 14K off the bumper. Most SRW 1-tons are not rated to pull 14K off the bumper, especially older ones. In fact, a lot of DRW 1-tons are not rated to pull 14K off the bumper. My SRW 1-ton is rated to pull 12K off the bumper and it's an '07 diesel.
My suggestion would be to investigate if your current truck could do a 14K 5th wheel and if so, switch to a 5th wheel trailer. That would be cheaper than swithcing trucks. If it won't then try a 5th wheel trailer and an older SRW 1-ton or dually if money is tight.
If money not a problem, buy a newer duallie and keep your trailer. Just make sure that dually can pull 14K off bumper. Many can't!