PHS, if you have the dough, try taking this problem to a sports medicine/rehab facility. They can give you a program to alleviate/stretch out your achilles and strengthen your leg muscles and walk you through the exercises to determine your specific weak areas. Once you target these areas, pain should be a thing of the past. I see high school atheletes daily working out in that type of facility using all types of drills.
There are those who give with joy, and that joy is their reward.