I pay insurance in a lump sum each year. Easier on the books than see it coming out of my account monthly. Most places will give you a slight discount if you pay for the year up front, or even 6 months at a time (like vehicle insurance). My premium is with StateFarm. I pay $1100 a year for my Durango, trailer, all equipment and up to 25,000kms of commercial kms. My vehicle insurance is separate at $900 a year. The key thing that business insurance provides is liability coverage. Say one of your staff decides to not watch what they're mowing, and gravel rocks spew through a glass patio door or large bay window. Business insurance is a must.