Maybe this doesn't apply to your situation but for others..
That's the problem. If he's just sitting there.. no insurance, no nothing, why would you want to hire someone like that? I'm not saying that you have to pay $1500/day for pushing over little trees (that sounds high for a small dozer) but don't get someone who will make a bigger mess. I'm not kidding when I say I get to clean up this stuff often. I've posted pics on other sites where inexperienced operators leave the customer with a bigger mess than they had. If the operator/business has nothing in the game, what happens when a fire gets out of control or they didn't call before they dig or push and the roots of a hackberry pull up a fiber optic line? It happens every day. A larger outfit here knocked all of our phones out because they didn't call before they dug.. and ran a dozer of the phone box which was inside a fence line. If they can do it, imagine what the little guy who is working for weekend money will do. Again, I'm not saying that you can't find someone responsible that will work cheap but make sure you get someone who won't screw you over.