Hello Max, it has been many years since I have skiied, and didn't have the incon to worry about back then, and yes, I fell PLENTY that first day. After a few hours it does get easier. I could go now except my back would be the one to give me the most problem, the incon I could deal with while skiing. It sounds like you have a great group of supportive friends, and that will help you in doing what you need to at stops and in the condo. Wear what works for you in your everyday activities, but add a liner or as Papa said, a second diaper inside the first, along with a good waterproof pant, and you should be fine. Be sure to post upon your return from it all and tell us how it went, and how sore your butt got!

Puffy