"if you want to consider yourself a competent roller in all reasonable circumstances, a highly skilled roller, an advanced intermediate roller"
I don't have a strong side vs. weak side roll, in practice or in real roll situations, so I suppose that could be taken into account. But that might be carryover from my having this same opinion when I first learned. I didn't "develop" my roll on a strong side before trying the other. One pool session I knew I had figured out the right hand roll I was going for, and the next session I used it as backup until the left hand roll worked the same. I practice both and use whatever seems most convenient ever since. Neither even feels more awkward to me - perhaps I'm lucky in that.
There usually isn't any consideration for me. The easier side to roll up on seems to reveal itself, though I have gotten confused and picked the wrong side on occasion. Because of this, I would suggest a person is better off not having a preferred go-to side to roll up on. Even if the person can roll up on their one side better than I can on that side, it would still be to their advantage to develop the other side to become more proficient in the situations where rolling up on the other side would, in fact, prove more proficient. I suppose the use of the word "proficient" may work well. Assuming there are times you want to roll up as quickly as possible - for safety, for air, for comfort - and it's quicker and takes less energy to roll up on one side than it does the other, someone well advanced in the art or practice of rolling (proficient) would go for the side that's convenient, not have to add effort and time to go to a specific favored side.
Kayak & Canoe Outriggers
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