Interesting thread here. Kina tells my story.
I do firewood and mowing on the side. I started small and grew it fairly large over the past 9 years.
I started getting into the insurance thing about 5 years ago as I was getting a lot more risky jobs. I have a general liability policy that covers my landscaping and me cutting up tree tops only on other peoples property that was just logged. 100,000 coverage for 253 a year. I have been thinking of upping this coverage, but my area is not so sue happy yet.
My truck and trailers have commercial insurance, as was stated before, your vehicle ins won't cover you if they find out you are working for dough and don't have a comm policy. This was only a little increase as compared to regular ins.
All my equipment is covered under a commercial inland marine policy and I cover about 35k for about 500 a year.
I don't lable truck for advertising, so no dot numbers on my risk. I also don't spray and chemicals, so no license. I know of many many contractors in my area who run on sole proprietor with no special license and no one ever has any trouble. Ever. I claim on my taxes and pay sales tax in.
When I talked to my lawyer, I was told that sole proprietor carries protection to the point of just what assets are solely in my name are at risk. Can't touch anything in my wifes name or "our" name together. And that a good insurance policy will cover almost all situations. A llc would do basically the samething, but cost some and carries more hassles and such, like having members and pretend meetings to "act" like a llc. In other words you only get legal llc protection if you "act" like a company and do all the mumbo jumbo stuff companies do. Such as meetingminutes, members, and so on. Since I am the only one, I stick with sole pproprietor.
When I started doing this, I stupidly thought Icould get just one ins policy to cover everything, and keep it simple. What a fool I was. It does get hectic keeping up with this bill, that bill, change this policy, fix that policy, check in on this, I thought I already paid that, and so on.
But all the insurance stuff is simple compared to dealing with people/customers. To me that aspect of business is the biggest pita. Don't get me wrong, I respect my customers and wouldn't be where I am today without them, and my business is doing great, but dealing with lots of customers (60 +) can get frustrating. Everybody is different and gets picky and that takes me more time and hurts efficiency. Charge them more for it and that opens up more issues.
To sum it up, there is so much hassle to trying to run a legit business, that if I didn't enjoy it as good as I do, I would just quit and watch andy griffith and dukes of hazzard on tv. (2 of my favorite shows)
To op, sorry to hear about your back and I wish you luck if you do try your tractor biz. It is like a roller coaster ride with some jobs making you want to pull your hair out and other jobs make you feel like you have found the coolest job in the world. You can make good extra cash and it can be fun. Take care.