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Approach, departure, and break over angles don't relate to hill climbing ability specifically. They relate to getting on and off the hill. The higher the break over angle (usually) means higher COG which includes weight transfer to the rear axle. Longer wheel base (usually) lessens the weight...

Ehhh? That's backwards. Without pictures it's tough to offer advice. Most machines that can navigate the hill would tear up the grass, if there is any. A track loader can get up steep hill, if the ground is firm enough. A mini excavator can get up a steeper hill, possibly towing a trailer...