[sambor]

First of all, CDL requirements are regulated by the feds but the states can add their additional requirements but not delete any fed requirements. The CDL is based on weights only and LEO's look at data tags on towing vehicle and towed vehicle for gross weights and add them for GCW total.
If you look at your state's website it will give you the info you need including all fed requirements as well as states and what class CDL you MIGHT need.

 

[sambor]

Does a 2500HD have a GVW over 10K? Mine was only in the 9K range if I remember correctly and the 2019 GM towing guide shows same.

 

[sambor]

Doesn't matter what kind of trailer or hitch type you use as far as CDL requirements. You need to look at GVWR on the truck as well as trailer. In your owners manual it will explain what the truck is rated for.
If your GVWR on the truck is 12,001 and you hook a 14K trailer to it, that totals 26001-- Class A CDL required.

Hook is correct as long as the truck GVWR doesn't put you over the limit. From what I see, the 3500HD's have a GCWR of 31K--

After all this conversation, I doubt that you would get pulled over for just weight. At least here in Texas I hardly ever see ranchers or construction drivers pulled over and those boys really overload the trucks and trailers.. When a 3500HD is on the rear bumps that is serious weight!

 

[sambor]

Go to FMCSA and read 383 for federal definitions and requirements for CDL's. The term "commercial" actually does not mean that you are making money using your truck just that it is over 26K.

As for the AG exemption, it only applys to vehicles being operated within a 150 mile radius and must meet certain requirements as to what is being carried etc. And IIRC it is only good for a crop season.

As you intend to pull your 5er, it might not be required for you to have a CDL because it is an RV which is exempt from the Class "A" cdl but your state might require you to have a "Class "A" license because of the size.

 

[sambor]

Well, you might have to get a medical inspection but usually that consist of you walked in, paid, and walked out with a med card. I took my driving tests with a 2013 3500HD ext. cab 4X4 SRW(GVWR 11,300) and a 3 horse aluminum trailer GVWR 16K. Piece of cake as long as you can remember how to parallel park with a trailer following you. Never did understand that requirement. Sometimes a CDL will get you a deduction on your insurance premium as well.