1.) I've spent a lot of time getting these boots to fit, so I am going to take them on the plane, as carry-on, to make sure they get there.

•  Our recommendation: Back packs  and  Boot bags   All easy to carry thru the airport and small enough for carry-on.

2.) I'm going to send all my stuff thru, as check-in luggage, but I am going to split my clothing between two bags. That way, if one bags does not make it, I still have enough clothing to get out on the slopes.

•  Our recommendation:  Cargo bags  and  Double ski bags   By going with the double ski bag, you have the room to pack one complete ski outfit and give extra padding to your skis.

3.) I'm just packing as light as possible and if a bag doesn't make it to the resort, I will just have to rent all my stuff.

• Our recommendation:  Bags with wheels   When using your cargo and ski bag, both on wheels, you can scoot thru the airport quick and easy. (This is the way I roll.)  

• Standard laboratory testing protocols define the performance of these fabrics. Water resistance is measured by the amount of water, in mm, which can be suspended above the fabric before water seeps through. Breathability or Moisture vapor transmission rate is measured by the rate at which water vapor passes through, in grams of water vapour per square meter of fabric per 24 hour period (g/m2/d), often abbreviated to just "g". In recent years some, but not all, sporting goods manufacturers have begun including this information on their product labels. Typical mid-range fabrics tend to have values of 5,000 mm of water resistance and 5,000 g of breathability; the best materials have 20,000 mm and 20,000 g.                                  Read entire article 

So in layman terms; the higher the number - the longer you can sit on a wet chairlift.