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.
2015 Ram 3500 6.4l hemi 4x4
BOSS 8'2" VXT
Hustler X-one 60" 3 bin bagger
Toro Proline 36" wb w/t-bar controls
Walker S14 36"
Shindaiwa T242, Echo trimmers, chainsaws, pole hedge trimmer, pole saw, hedge trimmer
Shindaiwa 633 and Echo 755