Loaded kayak - for me it rolls easier, the roll itself is slower. In general, when rolling one has to adjust actions depending on kayak's response
Rolling - yeah, wear a mask, whatever makes you comfortable. You are learning, why add additional discomfort of water running up your nose and eyes.
Flexibility - yes, some flexibility is required. There are a few elements to a successful roll, due to your possible limitations, you will need to figure out what works for your body. C2C, sweep - they might, or might not work for you - prognosticating over internet is more art than science. The only recommendation - find an instructor who has experience teaching a few rolls, not just one, be it c2c, sweep, or a particular Greenland roll.
Additionally - slow everything down, take everything one step at a time. If taking a class with other students, do not measure your progress on their achievements!
Hardshell Kayak Sail Rigs
Heel and Pegpads™
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