Since you know the exact days (and probably times) you'll be flying, go to Google flights and track all 25 flights on your airline of choice. After 30-60 days, you'll quickly figure out how the revenue management system works for that particular airline and route. Meaning, will the best pricing be 3, 6, 8 weeks out, etc.

Also, set an alert on those segments so when there's a sale, you'll know.