I think your problem with heelside is actually more a toeside problem. The proper way to use your toeside edge is to drive your knees toward your toes, pressing your shins against the tongue of the boot. The effect is that you'll bend you're knees instead of your ankles.
It sound like you are using plantar flexion (standing on tippy toes), which works your calves and once they're tired it is difficult to smoothly transition. You can pick this out on the hill you'll see someone hesitating and their heels dropping in an unsteady shuddering movement. Since snowboard boots are designed to essentially immobilize your ankle, it's a losing battle.
I had the same problem 15 or so years ago. I hammered through and learned to ride that way. I was compensating be counter rotating and swinging the board around. I had to correct the problem later on. Fix your toeside and the heelside transition will come much more smoothly.
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Last edited by baldylox; 01-28-2014 at 09:51 AM.