If you use a portapower, be sure to tee a gauge in-line so that you don't over-pressure the brake. A portapower doesn't SEEM like much, but they can put out a hellofalot of pressure. I saw a dumba$$ bust the park brake housing on a Case skidsteer this way once. I don't know about a Deere skidder specifically, but for most hydraulically released brakes, 150-200 psi should be plenty. I wouldn't go much over that.
If you're working with log skidders, pulling drivelines, etc., then you're probably aware of this... but having recovered my share of dead equipment, I'll make a suggestion. If this is a heavy machine with little or no brakes/steering, then you'd do well to chain a tractor both in front of and behind the skidder: One for pulling, the other for braking. Takes a little time and an extra guy, but it's much safer than running into the pull tractor.