This is a good topic. It shouldn't really disuade anyone from doing this biz except to make sure your bases are covered first. At least in my neck of the woods, people definitely spend a bundle on their decks. And there are lots of them. I just counted 16 of them in the next street over. There are probably another 75 houses there. I haven't found any without a deck. The numbers seem good.
Anyway, the realities of insurance are interesting. My father who has a general contracting company once had a roofing job that he got because the inexpensive roofer that wasn't a real company fell through the roof. (Ya know, they saved some bucks by hiring a friend of a friend.) He ended up in the hospital. Since it was right before a storm, they ended up with a $50K water loss. In this case the homeowner's insurance company sued the original roofer for the loss and gave the job to my dad. That "contractor" had lots of problems.
A few weeks ago I was talking to an insurance guy at church. We were talking about strange losses. One of his customers had hired a contractor PI to investigate one of their workers. They put the PI on a tractor of some sort as part of his undercover work. The guy proceded to lop half his foot off. The insurance company of the company that brought him in to spy ended up having to pay 1/2 million in liability because they found that he wasn't given the training that the regular employees had and hadn't signed off on a form stating such. A half hour training and a form cost 1/2 million and who knows what OSHA would do with that.
Pressure washers are dangerous. A good one will drill through a person or cut off toes and such. So you might remember the previous paragraph when you hire people. They can also easily poke through siding. So if you're not careful, you may be siding a house too. Also, siding is often damaged along the decking material by the owners. Might be good to always have before and after photos of your work for CYA and marketing especially if there are signs of previous damage.
Also, while there are some bad contractors out there in any of these service companies, who really mess with people, there are a lot that are unjustly raked over the coals. Do not underestimate the stupidity of the courts. There are a lot of scaremongers that make every contractor out to be a crook. They get their news stories or books sold that way. That can really hurt you because the courts are biased against any contractor. I talked to a friend of mine from way back that's a lawyer. He typically represents the cutomers in these suits. He told me that it's extremely difficult for a contractor to ever win. He admitted to me that even if the contractor was on the up and up, the people will always win even if they're scamming the contractor.
I've personally seen hundreds of thousands of dollars evaporate from contractors as people make up lies about different jobs. That's another story. At least these gigs are relatively small with little out of pocket cost.
One more thing, I did some computer work for a friend's company a few years ago. It was having some financial problems. He paid me, but he told me that his lawyer said he didn't have to pay me if he didn't want to. He could easily fix it since they were heading toward bankruptcy anyway. Luckily, he didn't do that since he owed me almost $15k for the job.
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