I'm not going to say that the utility requirement isn't crazy, but it seems to me that with a suitable jig this could be a 1 person operation.
We are talking about a pole weighing 160-200lb. Not at all trivial, especially if you loose control of the thing. The big risk is that you have the pole balanced in some nice fashion (resting on a headache bar) so that you are not actually manipulating most of the weight, and then something moves and you suddenly have to manage a bunch more force.
Start with the 'tilt the pole into the hole using the headache bar' concept. But instead of a pole resting on a bar, you have the pole locked into a jig with a hinge in place of the bar. Say the hinge is 7 feet off the ground and the pole is positioned 7 feet from the end. Now the effort is about half that of tilting up a 10 foot length of 4x4.
Then this jig would need to be able to release the pole in a reasonably controlled fashion, eg. using a winch or something similar. Ideally the winch could also be used for loading the pole onto the vehicle, but presumably you could get assistance with this at the lumber yard.
Just musing about solutions here, and the above is probably not a good approach, but hopefully it stimulates someone to come up with a good approach.
-Jon