Illinois is an expensive state to get insurance for doing tree work for either liability or work comp . Liability will vary and goes by your gross dollar income. WC is especially hard just for a guy just starting out with no track record, you will probaly get thrown into the pool ( high risk pool ) Last spring 's quote, I hope your sitting down $41 bucks / $100, minumum payroll $5000 add that to your overhead plus FICA, FUTA, IDES, (unemployment, which went up this year ) it is a little over 8% for small guys. Makes you do a double take when you see what you have to charge for just one employee on an hourly basis, makes you look like some high priced crook when you bid against others who don't carry any insurance of any kind.
I hope you got all your ducks in a row because if you don't your going to be be working for the goverment and the insurance companies, they could care less if you make money, but they want theirs. I used to run a bigger show than I do now, found WC to be a big drain on cash flow and downsized. We are incorporated family type biz so we can side skirt the WC, we are all legal owners and have certain percentages of shares in the corp, but I still carry the bare bones minumum payroll deposit to cover any part time help we may need in the busy season, if you don't use it you get a credit for the money and a refund which can be turned over for the next year.
Good luck on your new venture, maybe we will run into each other some time at some Illinois arbor function.
Larry