Joe knows more about the internal structure of the O'Day rudders, but my theory for cutting off the lower 9" of the 25 rudder would involve slicing it off 9" from bottom, then sand off and paint for about 6" up from the cut, the area should be roughed up to aid adhesion of the epoxy and fiberglass, then seal the open end with Epoxy resin, with that epoxy still tacky the plywood "wing" can be bonded to the bottom, then strengthened with a couple of layers of fiberglass cloth along the corner where rudder and endplate meet. The endplate/wing would then be sheathed in a layer of FG cloth to protect it. After the resin had all cured, the surface can be smoothed up and if the cloth pattern still shows, another light coat of resin be applied. Once that cures, and is sanded smooth, a few coats of a good marine enamel (or polyurethane paint) if the boat is trailered, or good antifouling paint if the rudder will be left on with the boat moored.
Perhaps, if enough 25/26 owners were interested, D&R could produce a "factory-made" version of this. That would reduce cost (versus a custom rudder) and ensure that it was built sturdy enough.
I wouldn't go with a kick-up rudder just to gain the 9" of reduced depth. I know of other solutions (besides keeping the rudder full depth and being VERY careful?) but I fear that your head is already spinning over my suggested "fix". Check out the rudders on the NIMBLE 20 and 24, I think they employ a "drop-plate".