I have been riding and teaching for many years and never came accross anyone not wearing a leash. If you think it will be ok.... It wont.... wear a leash and be safe. As far as Insurance, check out the IKO website and have alook at there insurance plans. Its priced at around $100 and is very comprehensive.
When you see shots in magazines of Pro's with no leash's this is generally when they are riding sliders for photo shoots etc in uncrowded spots. The reason for doing this is because if they fall on the upwind side of a slider and let go of there kite the leash would pull them straight into the rail and cause potential injuries.
Be Safe, Get Insured and enjoy our amazing sport
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