My 376 is very similar. I left Texas 6 years ago. Sailed to Bahamas, then Colombia, then Panama, then Cayman Islands, then Bahamas again, then the thorny path to Grenada, Then sailed west to Fiji. Boat can do the trip just fine. Sure, you need to keep the main in off the spreaders as much as possible and pole out the jib to windward, but you will not have any issues with speed on that trip, trust me. You will go as fast as you want. Lots of wind on that trip and it only takes 11 knots apparent to reach 7 knots in the water with the jib poled out, and 8 knots apparent to make 5 knots. You will not be able to go dead down wind like that so plan on staying AWA of 165 (no more)...sometimes you can do 175 but it depends on the waves. You can go dead down wind with just jib poled out but will need 15 knots true to make 5 knots in the water.
As for the rudder, yes, the stock rudder causes a heavy helm which is hard on the steerer/pilot and the wide stern can cause an active helm depending of waves, so my suggestion is to add at least an inch on the leading edge of the rudder. I added two inches and it is a perfectly balanced helm now. I can steer with 1 finger and be healed over 20 degrees doing 8 knots with 8 degrees of weather helm and when I let go of the wheel it stays put. My autopilot amps dropped from 3-4 to 1-2. IF you do modify the rudder, make sure you don't go too far. That will cause a unbalanced rudder in the wrong direction which is dangerous.
And yes, 356 is Class A and so is the 336.