Nobody is going to look at any drive time with a permit as being relevant as there is zero documentation to prove it. As far as any insurance company is concerned, you have been driving for less than a month, period. There is no way any credible insurance carrier will insure you as a driver in a commercial setting. In fact, you might find that you'll need to be 21 to qualify for such insurance since that is the age requirement for most CDL holders.
What sort of stuff are you driving exactly ? I'm not asking for the generic "1 ton dump and trailer" reply, but specifics, as in size and weight....Your "1 ton with trailer or chipper" isn't exactly light stuff, especially if you are loading it up with wood or wood chips. Depending on what size the truck is, a good load of wood and a trailer with a small skid steer could be getting close CDL territory....