G'Day Flintstone,
As you can see from RR's supplied link the conversion can be done. It is still working well on my Tandem.
There are two main aspects to this conversion:
1-Mounting the Rudder Mechanism to the kayak
2-Deciding on how you want the lines to work
As Hobie have changed the up/down line mechanism for the T&S on the AI and Adventure, if I was converting one now I would try to use the much improved newer system. I now have an 08 AI and I have fitted the upgrade to an 07 AI. It is a simpler line system that allows more positive lockdown and lift up. The AI line upgrade kit could probably be adapted to your Outback. You would have to add a pulley block on both sides in the bow for the lines to wrap around. As the Outback is shorter the lines would need shortening but I reckon it could be done.
Getting back to 1) though, you need to work out a way to attach the T&S mechanism to the older pull up system. The link details how I did it, though once again I would change some things if I was doing it again. I wouldn't cut the original lift up rod and I would notch the rudder for a better fit as RR suggested.
Hobie will supply the parts. I was surprised at how inexpensive the T&S with sailing rudder was when I first thought about this conversion so I ordered it in. You would also need to order a rudder pin. It made it much easier working out how to do it with the parts at hand.
Keep us posted
