Hi Cap'n,
I had great difficulty raising the sail the first season I sailed my boat (20 yrs old). Four things helped me:
-Change the halyard to a thicker, pre-stretched one - a stretchy rope is utterly useless for this.
-Change the top sheave which was pretty much jammed solid.
-Smear silicone grease the length of the bolt rope to overcome friction.
-Loosen off a couple of battens that were over-tightened.
any one of the above can sabotage you, and I had all four! No probs now though
Occasionally the thing used to just jam solid a few inches from the top, and that was down to having the knot holding the ring badly positioned, plus making the mistake that Gabriel warned of re. halyard on wrong side of hook.
I can heartily recommend SS Marine for advice/help with your rudder problem.
Hope you enjoy your boat.