f800 hotshot truck?

Hello there,
I am trying to get started doing just a little hot shot hauling. I have a 1998 for F800 with a 12v Cummins and a 7 speed Spicer. This truck has a sleeper on it and runs like a champ so I thought it would be a great truck to pull my 40 foot gooseneck. Primarily I want to be able to haul my own stuff like my excavator or skid steer or a load of building materials or whatever, but I also want to have the option to run to Jersey and pick up a truck for a buddy or haul a load of hay or even pick up a quick load off u-ship or something. So basically my dilemma is that I don't know if this truck will work out legally because it is 28,000gvrw and I don't know what plates and insurance it is going to take. I live in NY and am just trying to get into the hotshot gig, not full time but maybe a weekend here and there to start and see how things go. But I cant really afford to do apportioned plates and road tax and all that right off the bat. Is it legal to register the truck with new York commercial plates? or does that mean I am bound to New York? or can I register it for under 26000 and be ok? Its not a career for me, I just was thinking that if I was to go to Florida to pick up a piece of equipment for my self, it might be nice to take a load on my way so I didn't have to run empty $$$$$$. Well any advice or input would be greatly appreciated. Thanks. And p.s. I don't have a valid class A and med cert card.