Being without our boots is not a chance we are willing to take when we're going on a ski vacation.
Also, I have been on many business flights when there was no overhead compartment space left due to oversize and sideways bags, and after the maximum overhead capacity was reached every new boarder had no choice but to have their "carry-on" bags go into the cargo hold, regardless of size. I have many times seen flight attendants turning sideways bags 90 degrees around, and once even seen two flight attendants remove several bags that were "too big" from the overhead compartment to make room for others.
We often travel one leg via smaller "Regional Jets" like the Embrair and Canadair Jets, which all definitely have less overhead compartment space than the Big Jets, and depending on the model number can have overhead space quite smaller than the "maximum size" measurements. Often on those flights they let you "Gate-Check" your carry-on bag that won't fit, and that's OK if you get it back on the Jetway on the other side - unless waiting for it on the Jetway then slows you down and you miss your connecting flight, or they decide that everything that was gate-checked is just going to the carousel with all of the other bags from the cargo hold (had all this happen numerous times flying for business).
I also highly recommend paying extra to be on an early boarding group, as that virtually eliminates the chance that no overhead space will be left when you board - when traveling on vacation. For business I wouldn't pay any extra since I wouldn't be able to expense the upgrade fee, and it ends up being just another inconvenience of air travel. Lately when I travel the last boarding group has lots of people who get no shot at the overhead space.
All valid points.
All I'm saying is that the Dakine Boot Pack works just as well as the textbook "22x9x14" roll-aboard carry on suitcase. In all of those situations of regional jets or full overhead space, a standard carry-on suitcase would be screwed as well. Short of Fed-Ex'ing your boots or finding a way to fit them underneath the seat in front of you, it's one of the most reasonable options.