A guy that goes to my church has a small construction business. He has a 45HP Deere 4320 tractor with backhoe and FEL. He gets $50/hour for running this machine. He paid $24k for the machine. I had him over my house last summer doing some work. $200 for 4 hours worth of work. In the winter he is running a F-250 truck with a plow doing snow removal, big V-plow blade. You have to determine the type of work you will do, you will need to have insurance if is anything considerable. Grading a driveway for $60 or $80 is nothing. But it would be semi-safe to do without insurance. I wouldnt dig holes, or do heavy landscape work without insurance. Keep in mind that the insurance bill will be minimum of 10% of your sales. I had 2 excavating contractors tell me this. As far a skid steer loader, a good one is likely $10,000.
A guy I know used to do side jobs. He was asked to quote brush hogging a 10 or 15 acre field that was a fricken mess. Waist high weeds, rocks all over and ant hill mounts. He and a buddy quoted it at $4,500 and they got the job, no one else would touch it. They made a killing, they got lucky. It took a week to do. They had to rent the tractor to do the work. I wouldnt want to mess with it, possibility of running over a wire fence with a rented machine etc, hitting a boulder with the brush hog. It depends on how lucky you get.
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