The blade is forward of the shaft when you paddle. So, it "trails" the shaft so to speak. Gives a nice solid feel in the water. I suppose, it depends not so much on the shaft but on the blade - I have the Kinetic blades and the "trailing" effect comes from the blade itself (so you would have it on a straight shaft too, not just on a bent shaft).
As for a second hole, I would think twice - the way the Lendal lock works is that as you tighten the little bolt, something expands inside creating pressure outwards. If you have too many holes you might potentially crack the paddle. On the other hand, you don't need too much force to tighten, so it might not be an issue in practice...
If you do decide to drill, wrap in masking tape first to minimize the chances of scratches and chips from the drilling. A sharp regular drill bit should work. Or you could use a dremmel or rotozip as they will drill nicely, but with these it might be quite hard to get the hole where you want it.
Kayak & Canoe Outriggers
Classic Freestanding Rack
Wall Mount Boat Racks
Touring Kayak Paddles
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