All that I will say against your post is that maybe your geographic are in the great lakes has a lot of large accounts, that first timers can get a hand on but more likely you won't get those big jobs. To buy a 36, 52, 72 and equipment your talking about $20k easily.
There is an Old Blue Chair for each and every one of us, we just have to find it.
2006 GMC Sierra 2500hd crew cab
BOSS 8'2" Power V
Hustler X-one 60"
Toro Proline 36" wb w/t-bar controls
JS46 22" walk-behind (wouldn't recommend)
Shindaiwa T254, Echo trimmers, chainsaws, pole hedge trimmer, pole saw, hedge trimmer
Shindaiwa 633 and Husqvarna 130BT blower