I got the hails from last year and they...
I got the hails from last year and they hurt the side of my leg right above the ankle. Do I need a softer more flexible boot?
A softer flex boot would probably help, but first you should experiment w/ different binding stances. Mess around w/ your stance angles to see if that alleviates the pain or not. I'd bet that your stance is partly the cause of (and solution to) that pain in your lower leg.