Yes you need the home improvement contractor license. A single fall clean up will normally but you over the 200 dollar job number. It's not a big deal unless you have a felony in the past 12 months but even then they will do a hearing for you.
You will want business insurance to protect you from liability. 1 mill per 2 mill cap is a good standard policy. You can opt not to have insurance on your equipment but if it gets stolen or you have a fire you will find your self instantly out of business.
We have combination plates in the state as well as commercial and you can have either on a pick up. But the commercial has negatives you can't drive on the park way and it expires every April where the combinations go 2 years no matter what month you first registered them. Also it cost like twice as much now on the trailer you want commercial it took us 8 years but one day I found a cop with no life or anything to do and man did that day suck along with the dmv trip that came of it.
As for vehicle insurance business is better and your find it cheaper in most cases too. I pay about a 1000 a year per truck with little difference in cost between the old 89 3500 and 99 3500 too the 2011 and 2012 4500s that cost 60-65k each. We do full coverage with 500k on the vehicles.
Tax purposes you can do the local town thingy for the sole proprietor or you can go the state rout and incorporate.
Workman's comp is the one we went with out the first 2 years the quotes we got were ridiculous and they wanted the money up front. Year 3 we were finally able to get it through our payroll company that uses the Hartford. The nice thing is no up front costs at all we pay a % of what the guys make and that is taken out as we go each week. The cost on that is nice now only 4.5% we have it on all employees but we do not keep it on our selves. As an owner you are not required too but you may run into a commercial account that requires you to have it if you want the job.
I wouldn't bother registering the truck in the business name but all trucks you buy for it from this point on you will want to do that.
But before you get to do any of that you need your name and either the state or town has to sign off on it depending on how your set up. You can't really do advertizing with out a name you can't open a business checking account with out the name. And you can not get your sales and use permit with out the name. So that is step number one and get on that now we got held up nearly 2 months our first season because of some mix up in the paperwork. And that was the good old days under Bush in Boom times today that delay in spring would be fatal.