I started out young, probably earlier then I should of. When I was in like 5th grade (2001), I was doing 4 or 5 neighbors places with Dad's 311 Dixon and commercial John Deere trimmer. The next year Mom bought me a Toro 21", and I bought a John Deere handheld blower. Year after that I went 50/50 with Dad on a brand new 3303, 30" Dixon. Then in 2006, I bought a brand new 44" Dixon, then the next year traded it for a used 50" Dixon, and also bought a used Walker. This year, I added a new 52" Grasshopper. Over the years I have bought a few edgers, a bunch of trimmers, and a few blowers. I am FINALLY at the point that I have about the best lineup of equipment possible for the lawns I do. Only thing that will make it better is buying my friends Dodge 3/4 ton flatbed dump truck.
I graduate HS in 2 months, and plan to be doing this full time for the foreseeable future.