#2 started with small mowers....2 21inch Snappers
2 Stihl backpack blowers br420
Echo hedge trimmer
I got a loan for $3000 to cover all of this and to cover cost of flyers. I already had a truck. All of this was paid off within 6 months. As soon as there was not enough time in the week to get it all done, we stepped up to a riding mower. We soon outgrew that and stepped up to an exmark walk behind(48 inch), and then eventually a Laser Z(48). I highly recommend this approach and for these reasons
1) It keeps costs down
2) It gives you goals to reach for early on. Work harder and faster to get that more efficient and easy to operate equipment.
3) It conditions you to be able to handle a heavy work load. I would never now cut 30 average sized lawns each week with a 21incher, but I do know I could do it.