That straight mast will require inching the tractor forward as the hole is dug. PITA!
I imagine you have similar gravel soils to mine, and that will definetly require several in & out's of the hole. I do it with my SS where the visibility and moving the machine back & fourth is simple. If you have hystat trans, that will be a big help. A pounder should work with your machine, most have a small cyl. to lift the hammer back up and do not have big hyd. requirements, the post takes the impact and some sit on the ground for the entire post driving. You'd be suprised what a sharpened post will push out of it's way. I used to have both and sometimes would drill a small (4-6") pilot hole then pound the post in in tough soils. I actually used an excavator to push them in, but same theory. No pointing the post with a pilot hole.
Is it worth hauling your tractor up to the guy with the pounder for a "test drive"? I know you said you can't do both, I'd start with the pounder. Another thing, The phd looks like it is direct drive. The one I have is chain & sprocket off the hyd motor for a mechanical advantage. The better models have a built in Planetary gear set up directly off the hyd. motor. Either way, both use a mechanical aid for power, just an observation.
edit; Oh, no down pressure. I was thinking how my phd works on the SS, that definetly makes me confirm my vote for trying the pounder first.