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you may need to do a bit of research into your local/state regulations and actual enforcement practice.
you've got a couple of areas of concern:
1) having a rig that can exceed the weight limit for a regular driver's license instead of a CDL. Some states don't pay much attention to casual commercial drivers and weights … others do, looking for commercial weight/equipment/licensing requirements and log books, etc.. The key here in some states is not the actual weight of your combination, but the max weight rating total of your truck and trailer. For example, a 3/4 ton pick-up and a modest sized trailer, you may find yourself with a 24,000 lb (or more) rated combination.
2) hauling for hire puts you into a commercial category instead of your personal vehicle insurance. The minute you advertise your professional services for hire, you've crossed the line from a private vehicle operator to a commercial hauler charging for your services which could also be a trigger for requiring a CDL compliance.
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