However, this family business has been in existence for 60+ years. I don't think that starting a new tree cutting business and going head to head with them will be nearly as profitable if at all, because you wouldn't have the same contacts and good will that they do. Contract work is often a word of mouth and referral business, not dissimilar to the legal world.
I totally agree that such small business owners can make great money. I recall from The Millionaire Next Door that many of the "millionaires" profiled in that book have the unsexiest businesses that they'd been working hard at for decades, saving wisely. I do know of an electrical contractor that worked on our house a couple of years ago has a healthy, very profitable business going on. But I think there's more than what immediately meets the eye, and just going into an unsexy business for the sake of going into an unsexy business is not a sufficient condition for financial success in one's business.