The only thing I regret doing my first year was investing over $9000 into a lawn care business before I had lawns. I couldn't claim any of my expenses because I didn't make over what I spent on purchases. My advice would be to invest in a used walk behind with bagger and 21" mower and good string trimmer, Stihl blower/vac combo and good trimmers for shrubs, some rakes,and tarps and you'll be able to tackle most any job till you get a good customer base.