If you are in fact a teacher, you'll likely be booking around school schedules. If you're not willing to be flexible on destination and book either at the last minute or 10-11 months in advance, your best bet may be to simply collect signup bonuses and then cashback or points in a program like Arrival card. The first step for everyone deciding what program to concentrate on is to spend a few hours doing dummy bookings. Award charts mean nothing if there are no seats available or massive surcharges will be levied. Click through until you see the cost in miles and the taxes & fees. If you share your 'home' airport and the trip(s) you want to take, you will get better and more specific advise.