Nice job loading that by yourself. It is a gamble to leave the skid steer without the bucket locked. Mine is the same way.
Used to have the same problem working by myself with less than perfect situations. My newest strategy involves a winch with a wireless remote, ramps on the trailer, and skid steer. Now my son is using the system and loves it. The real reason for the winch was to load the skid steer on the trailer in the snow. Now it pulls up combines, tractors, cars, and trucks with flat tires without a problem.
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