What should I buy

[Ryno1]

Since she has a dump bed on her pickup and can drive it up the hill, I'd suggest a tractor with high fel lift to load the pickup, then for the small planting holes add a posthole digger or backhoe to the tractor. Only time you would be taking the tractor up/down the hill is to make planting holes.

Going this route you can find what you need in any brand of tractor, that allows you to find a local dealer that you trust. Seeya Terry