I have a high school friend who got his CDL recently and mostly picks up flatbeds for Lowe's (he got his experience from driving tank carrier trucks in Iraq). From what he talks about, the long hauls are what you want, but he gets a bunch of short runs that don't earn him enough. He's on the road a lot, but I don't think he really likes any of his kids (except his oldest daughter, but she's leaving for college) so it kinda works out for him.

There's a guy in our city who has one of those machines for grinding stumps. That's literally all he does. He's gotten in with several tree cutters, grinds stumps all week long and makes enough to sustain his business. So a wood chipper might not be a bad route, but you gotta find companies that really need one, offer a good price and really establish yourself. It could pay off, but it's a lot-o-work.