My truck is under 7k curb weight, and under 10k GVWR.
My trailer is under 4k curb weight, and under 16k GVWR.
My total weight is 10-11k, and under 26k GVWR. If I am reading the law right, if my truck GVWR is over 26k, CDL A required. If my trailer is over 10k, CDL A required. If my combination GVWR is over 26k, CDL A required.
So at least by my trailer, if I'm pulling in a commercial manner, I am required to have a class A CDL? I am looking at starting here shortly, and I want to know what I need to do, or if anybody is offering up any hot shot jobs as well. If I need my CDL A for this, or even my CDL B, how do I get my license?

To be able to get my license, I need to have a properly registered and insured vehicle in the class of which I am obtaining my license for. Being that this will be my pick-up and trailer, I need to change the registration to a commercial combination and obtain Commercial Vehicle insurance on my truck. If I do this however, I could not drive my truck and trailer after I change the registration to being a CV without having the appropriate CDL. I get the easy way to do this would be to have another CDL driver drive my truck for me to the DMV for me to test, but my wife and I don't have any friends or family nearby, and we don't know anybody with a CDL. Any LEGAL suggestions on this?
If I am not mistaken, I have to take the truck/trailer to wherever I register it at since I'm changing the registration type. If I didn't have to, I might consider hauling another truck on my trailer, and unloading it in the parking lot of the DMV, and driving the second truck to the registration office to have the registration changed, and then get my proof of insurance with the new registration. Then I could return to the DMV to take my driving test. I'm not sure how else to do it.
Thanks guys!