Are you sure its your skis that are squeaking? It could be your bindings, I have a pair of Jesters that squeak from time to time. On how hard is it to break a ski- as mentioned above it really depends. I have four buddies that all shred pretty similarly in the park- very hard. Two of them are always snapping tails and needing new skis, and the other two have never broken a pair of skis besides edge damage. A lot of it is just luck (or lack of), but try your best to not land too tail heavy. Land then afterbang, don't land in afterbang.