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My only concern is that with many jobs there would be larger debris that a small chipper couldnt handle, with a large dump trailer like a 12ft, I would be able to chip up what I can and just throw the rest on top.
I think I'll buy a dump trailer first and just dice up debris until I can afford the chipper. At least it will save me from pulling it back out of the trailer (the worst part).
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I'd try to develop a network of people that want to pick up rounds and branch wood.
You might find some retired guys that would love to get out of the house and load some limbs that are too big for a small chipper without the weight of heavy rounds. They can go home and play with their chainsaws. Even if you help to load limb wood into their P/Us or trailers, you don't have to unload or process it.
When there is firewood left for the homeowner, spinning a greater amount of firewood that just has to be seasoned longer than split wood, rather than splitting the wood, can be a good way to go.
"Wood's going for about $xxx/ cord. If I cut up the limb wood for you, you'll end up with about an extra 1/2 a cord."
When I'm trying to encourage them to keep smaller wood, I'll explain that limb wood is good, dense wood that many people overlook. I tell them that I might heat my own house with 1/3 limb wood, selling the extra rounds. They see value in it. I'll say that generally we chip 4-5" and down, and cut 4-5" and up. Then I show them with my two hands, thumbs and index fingers making a circle, what 3", 4", and 5" looks like.
Sometimes, people seeing that others see value in limb wood helps them to see that it produces money saving heat, same as split wood, and you can simply fill the spots in the firebox between split rounds with limb wood before turning in for the evening, resulting in greater likelihood of having coals in the morning to be able to just add wood, rather than rebuild the fire from (expensive when purchased) kindling and fire starters. Small limbs are easy to split in half for starting the fire, too.
Spinning it honestly can be win-win.
This sometimes means that I can drive my p/u (12 mpg) and trailer 30-40 miles round trip, and run errands en route, rather than a large dump truck (4-5 mpg) and chipper. As well, you can sometime drive the p/u and trailer right up to the limbs, rather than dragging them further.
Sometimes, this means a significantly better profit on little jobs for repeat customers.