I'm only gold these days, so I'm very aware of all you platys ahead of me. I've got 13 upgrade certificates left over that I can never use.
Monday mornings and Friday mornings are the serious business travelers. ( you will know them because they don't look lost in the airport)
Usually I carry my boot bag on when I am going skiing, although my luggage is almost always on the flight with me when I arrive to my destination . When it isn't the airline sends it to me by courier within 24 hrs and it usually makes it in the middle of the night. Chances are very slim it doesn't make it in one day ( I did have a flight to Russia one time that took 4 days for my luggage to catch up, so if you are planning a ski trip in Russia I would carry my boots on.)
I've never permanently lost luggage. I don't remember ever having late luggage on a business trip. But we usually had delayed luggage back when we traveled at Christmas time.
I have had skis delayed a couple of times, losing a half-day skiing the last time. (If we had been in a hotel, I would have rented for the day, but I was afraid they'd just be left out front at the condo, so I waited.)