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The federal requirement is only applicable when engaged in interstate commerce. And it kicks in for even a pickup truck with a 10,001lb trailer if you are in fact engaged in commerce. In AZ for example, antique military vehicles are specifically and explicitly excluded from requiring a CDL...

You've made a bunch of assertions that are specific to California and even more specific to your experience within California. They don't apply elsewhere. They're merely one data point on a spectrum of data points. Many states don't require anything but a normal driver license for a...

Maybe, but they're going to hate it. It's really not similar to modern commercial truck designs. I'd rent a truck and trailer. Give them something plain vanilla that they're used to dealing with.

Air brakes would be a direct connect, and possibly provide springbrake emergency brakes as well. LED lights would allow for using 12v or 24v. I haven't compared deuce pintle height to dump truck pintle height. It's going to be at least somewhat close or better.

Either of the two trailers I pictured would tow dead level. Electric brakes and lights would need some tweaking.

This kind of thing? What size tires on the deuce?