From a designer's perspective, there is an axiom with rudders -- use the least amount of rudder to do the job. The principle behind this is that excess rudder surface creates unnecessary drag. Hobie apparently subscribes to this idea. The small Hobie rudder in most cases, is adequate to control the boat, and actually turns the boat better than most other kayak rudders (which are largely even smaller). But then, most paddling kayaks have the paddle available to readily assist the rudder when necessary.
When the Oasis got its new bottom, it lost some rocker (and therefore some turning ability) and gained 100lb. capacity, so the boat doesn't settle in the water as much as with the older Oasis. In other words it lost some of its steering capability (especially on swells). In this picture, you can see how much of the small rudder is now out of the water from it's high mounting position (new Oasis on left, old on right):

Thus the desirability for the deeper reaching large rudder.
I have not operated an Outfitter or the Outback with the large rudder, but my experience with large rudders on the Adventure, Oasis, Revolution, Sport, i-9s and i-12s are very similar to jeep's description. Certainly some of the Hobie line needs a large rudder more than others, but I believe they all benefit greatly. It's like getting performance tires and shocks on your car -- the handling improves significantly. The slower the speed the greater the difference in authority, right down to 0 MPH with the large rudder. The higher the speed, the more stable the tracking and with fewer adjustments with the large rudder. I've noticed this to be universal with the different kayaks. Additionally, for both tandems and inflatables, the turning moment is slower because of the greater weight and/or windage factor, and the large rudder compensates for this to some degree.
The first thing all my Hobies get is a new large rudder. With all respect to the designers, the benefits of the large rudder outweigh any friction losses. In fact, I was in a race a couple of years ago against a much superior athlete (identical boat models). Luckily, I had two advantages -- Turbofins and a large rudder. If he had either one, no doubt he would have won easily. I spent a good part of the race looking at the back of his head (and boat) and noticed his boat wiggling as it wormed its way through the swells, his rudder in constant motion, slowing him down fractionally with each adjustment.

My large rudder kept me on a straighter track. Fortunately he doesn't follow the forums often (and I keep "forgetting" to divulge this to him) so there is an excellent chance he'll keep using the small rudder (heh heh)!
I am totally spoiled by large rudders and consider it a severe handicap not to have them on my boats. Just as most cars don't come standard with Bilstein shocks, most Hobie don't come standard with large rudders. But at least they make it economical to make the upgrade. IMO, it's the best $23 accessory Hobie offers.
