To be honest most of us have little or no experience in what you are doing. We know a lot about commercial issues, but what you are doing is new to us.
I suggest you call the DMV, insurance companies, etc and ask your questions that pertain to them.
I would think though, that renting as needed or buying a 2nd straight truck would be a lot cheaper in the long run than the upkeep of a tractor trailer. You also would have less worry about low clearences, restricted routes, getting in and out of your destinations, etc.
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Finding the right trucking company is like finding the right person to marry. I really comes down to finding one whose BS you can put up with and who can put up wih yours.
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