We just purchased insurance and went 100% legitimate about two months ago. Just felt out the water for the first 6 months (neither myself nor my partner used this as income for survival in the beginning), and discovered that there is plenty of money to be made. Invested every penny we had into buying equipment, and got things rolling and decided to make everything legit. After reading up on here some, I went into our local Nationwide office and checked out what they offered. The best rate was subcontracted out to Tapco Insurance. Got us a $2,000,000 liability policy ($1,000,000 per incident, $2,000,000 per year) for ~$750. I paid it in one lump sum up front, which dropped the price a little bit. If we divided it up over the year, it was somewhere near $1100 per year, or ~$100 per month). That is for coverage of us in Virginia, with only 2 employees and no bucket truck work, and an expected income of ~$100,000 per year. It covers us for all work from trimming, to pruning, to felling, and removal.
~Will Courtier~