I think the idea that skegs are for tracking or that skegs make boats hard tracking is kind of a mis-conception, that misses the way a skeg is designed to help.
If your boat is tending to turn upwind, or if you need to make downwind turns, lower the skeg a bit more.
If your boat is tending to turn downwind, or if you need to make upwind turns, raise your skeg a bit more.
Skegs aren't primarily intended to make boats harder-tracking, they're there to change the trim in wind.
If you're sweeping a bunch to turn in windy conditions, play around with rudder strokes at the bow and stern. Try doing upwind turns with a bow or stern draw. Then try a downwind turn with a bow or stern draw. I think you'll find that one really does well turning up wind, and the other really shines turning downwind. You can link these with sweep strokes, and the difference over a sweep alone is impressive.
2-3 Canoe/Kayak Trailer
Classic Freestanding Rack
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