No two runners' overuse injuries are exactly the same, but there are some generalizations that can be applied to prevent future overuse. Let me start with the most serious one in your situation first. The fact that you have had stress fractures (plural) is a bit worrisome. An initial stress fracture may be attributed to training errors or flawed biomechanics, but a second stress fracture probably deserves consideration for a medical evaluation of the athlete's bone metabolism. A primary-care sports medicine physician will probably want to check several blood tests, since there are systemic bone problems that increase the risk of stress fracture that may be reversible and treatable. One common issue for New York runners is low vitamin D levels.
Most running injuries occur because of overuse, and overuse usually occurs as a result of a training error. The challenge is identifying your training error and avoiding it next season. Think about when your pain started and what you were doing for run training at that point in time. More often than not, runners ramp up their training too quickly, which results in injury. Rapid increases in distance, intensity (speed) and hill running can all increase risk. Increase each parameter individually, one at a time, and think about ramping up half as quickly next season. Running no more often than every other day allows for recovery of damaged tissue between runs. Finally, a flawed running gait may also predispose to injury. Having a trusted running coach evaluate your running biomechanics may be worth considering, as well.
Dr. William W. Briner is a primary care sports medicine physician specializing in the non-surgical treatment of acute and over-use injuries in active patients. Dr. Briner has served as a team physician for the WNBA Chicago Sky, the U.S. national soccer teams, and several high school and college teams. He is currently the head team physician for the U.S. national volleyball teams, in addition to chairing the Sports Medicine and Performance Commission for USA Volleyball.