My first inclination would be take the rudder off and use epoxy and glasscloth to repair the damage from the outside; then I'd try paddling without it. If that went well, problem solved.
If the rudder has to stay, the biggest challenge will be getting at the inside of the stern to repair and reinforce the damaged areas, and then reinstall the rudder - that's a long reach back there. Maybe tape up the outside, stand the kayak on end, do an end pour of epoxy, redrill the bolt holes from outside, then find a way to hold a nut and lock washer in place inside while you tighten the bolt...be a fun project! Think multiple socket extensions, and a friend with long, long arms.........
2-3 Canoe/Kayak Trailer
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