I have 16 lawns or so that I do weekly. I drive a 2003 GMC 1500 and tow my equipment on a 6x10 trailer. I have commercial insurance on the truck and trailer, general liability to cover the business and an inland marine policy to cover the equipment. If the equipment is stolen, and you don't have inland marine coverage, your SOL.
Call your agent and/or call a few and get quotes. prices very dramatically from one company to another so be sure to check them all.
Just like everyone else on here, I have stuff that cuts, whacks, mows and blows. And way to haul it around.