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I started out by subcontracting for a larger company with my pickup. It's a good way to learn the business and make a few bucks at the same time. After a few seasons, I began to build my own business and then later broke my ties with the larger company.

Common sense goes a long way in this business and your post suggests you have a fairly good dose of that in place. I wouldn't take a fairly large commercial account on as a first attempt at plowing, give yourself a couple seasons or more to learn how to handle snow and ice, then jump in with both feet!
 
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