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This may have no relevance to a Harley at all but I've had two Triumphs with kick starters and they will definately break an ankle if you're not careful. The procedure I was taught, along with spitting over my shoulder, was to hold the clutch in and kick it over a couple of times. Like I said probably don't mean squat for a Harley but you might give it a try.
are you trying to kill the guy? If he holds the clutch in hes going to break his leg if he kicks with some intent, you see that dis engages the motor. he will be kicking over tranny gears and thats it. Sounds to me like clutch is slipping and your not getting a full kick. tighten the clutch or replace or clean discs. Happened to me on my 103, and it needs every bit of kick to get going. a little slippage and it wont go.
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