Just a heads up, since I recently went through this. Any trailer over 10k lbs needs a class A cdl, and the truck needs licensed in combination and depending on what your foing you need dot numbers as well. Yes most the farmers are illegal, but most the cops won't say anything, or don't know all the dot laws. I recently purchased a 14k lbs dump trailer. Haul it behind my 96 f-250. The gross combination weight of the truck is 18.5k lbs, so I thought all was good. I got pulled over on my way to the dump, I have my class A cdl so I thought I was in the clear. Turns out I needed the proper combination weight for the truck to include the trailer. (This is all for personal use. Didn't want to buy a dumb truck so figured the trailer would be easier.) Anyway. I had to call my uncle to come get my trailer as I wasn't allowed to move it without the proper registration on the truck. The dot cop was nice enough to explain this all to me wile he wrote out my fine. The almost $600.00 registration fee was less then half the fine I got. Federal dot laws trump all state laws. Just so happens they are getting money hungry around my area and pulling everyone with a trailer over here lately.
This also includes the farmers. Friend of mine does custom harvesting. Never had his cdl, because he was farming. Turns out when he's hauling for another farmer for profit, you now fall into the commercial side of things and not the farming side of things, as it wasn't his "product".
You really need to check the laws before you decide to buy bigger. There's a lot that have changed recently amd non of the new laws benefit the common guy just trying to make a living.