We are doing this in the opposite direction (NY to LA & Cate) and have a year of travel under our belts. One thing that I did which may or may not be helpful, was to try out a few different options that first year. Different airlines, airports, times, transport between airport/school etc. It was trial and error to be sure, but my DD now knows exactly what works best for her. In June, I booked all of her flights for the coming year (yes, I’m a freak!) But I was able to get good prices on the flights that she wanted.