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Also don't be afraid to borrow money i.e. a loan from a bank.

Personally if material is fairly easy to get rid of I would go: truck, dump trailer, and mini first. A chipper is just that a chipper. A mini will feed a chipper, move wood, dig driveways, dig patios, dig sidewalks, load logs, lift heavy things that you can't, plow snow, plant trees, and clear...