John, What the home owners think of you will determine if you get hired or not. So it does matter a little. This however does not mean you have to show up with all the newest equipment and maxed out credit to match. Take your time and grow as you can. If you have a push mower, trimmer and edger and a blower you are well on your way. I would make sure to get entry level commercial grade handhelds if you can swing it as they will hold up and be a good investment in the long run. All said new this will run your roughly $1500. Although this is a big investment at this time you should recoup your money quickly. As you grow - a walk behind mower or a smaller Zturn maybe needed. As I think I stated before. If all you have to start out with is a push mower, try to get the handhelds and blower, then use your lack of a bigger mower to your advantage. Market yourself as one that push mows lawns with a small residential mower. There is a market out there for those that think the Zturns up there lawn. With this people they will be willing to pay a little more than the average for a lawn service. This is your niche. As you grow save money and invest in a walk behind or small Z turn - something in the 34 or 36 inch size that allows you to still get into small gated back yards. This will allow you to be quicker and more profitable vs you push mowing accounts most likely. That is just my suggestion to get started. Work with what you got but do get the handhelds as trimming and edging are something that most home owners will expect to be completed. Then everything else is grow as you can. One last piece of advice. Do not go out and buy all the expensive equipment and trailers until you know that this is going to work for you and that you will enjoy doing it.