Technique is usually the thing that will make this work easier. It is also possible that the control lines are too tight. I wrote an FAQ on it that your can find here (top topic of these forums).
<<1- Techniques for easier rudder system use.
Hard steering in either direction can cause excessive friction in control lines. More centered steering will make raising and lowering operation smoother.
Deploy rudder: Turn steering handle to left. While actuating the down rudder control handle, steer the rudder right. This helps to move the rudder weight/mass in the direction required to begin lifting it off the deck. Actuating the down control while the rudder swings through the center position will work the best.
Retract rudder: The rudder has a small catch / indention to help keep the rudder down while in use. By (quickly) wiggling the steering (near the center steering position) back and forth while actuating the up control, the rudder is more easily released from the catch and raised.>>
See the complete post here:
http://www.hobiecat.com/community/viewtopic.php?t=6943