I don't think there's any secret to it - just find the cheapest few airlines, before the bag fees, and then find out what their bag fees are to see which is truly the cheapest. $75 higher airfare with $100 lower fees is still a net savings.
I take my boots and helmet in my carryon. A helmet is worthless if it's been dropped hard or crushed, and if you check it you have no way of knowing if this happened to it during transit. This may be a bit extreme of me, but in my opinion therefore a helmet that has flown as checked baggage is a worthless helmet. (That being said, I once fell while getting off of a plane, twisted my knee, and landed on my helmet which shattered it, so I guess I can't win.)
As for carrying on the boots, it's just that I paid to get custom footbeds, so darn it, I want to use them. If my checked bags get lost, I could rent skis, fine, but I can't rent boots that fit my feet as well as my boots do.
Edited by chase - 10/15/11 at 7:50pm