Derek,
I just went full time in my business this spring. I used to be a engineer sitting in a dark, boring cubical. So far, I am doing a lot of land scaping, dirt grading, replacing bushes, mulching, driveway grading, bush hogging and assorted stuff. I purchased insurance for my business and it was around $1600.00 per year, full coverage on all equipment. I have a JD 790/FEL, 6' grader blade, 5' box blade, 6' landscape rake, 5' bush hog, JD 335 Garden tractor/54" deck, assorted hand tools, line trimmers, blowers, 18' 12000# tandem axle trailer, 12' 3500# single axle trailer and my 26' x 40' arch building, since it houses all my equipment. Make sure when you talk to your insurance guy that you tell him where your equipment is stored. My home owners insurance policy would not touch my arch building, since it stored the business equipment. If you had a fire where you store your business equipment, and the existing structure was insured under your home owners policy, your home owners insurance may "burp" on you when it comes time to collect on a claim. They can legally do that! Also, don't forget your county or city business license. You will need that to be a reputable business. Get you a good landscaping software, also to run your business side of your operation. Very valuable tool for about 300 bucks. E-mail me if I can be of any help to you. I live in the Middle Tennessee area, which some areas are flat, some are extreemely hilly. Some projects I refuse to take on right now, based on the hills are too steep for my 790. Might have to look at some of those hill side mowers!