We have pulled the mast every year on every boat we have owned. Our boats are stored right on the shore of Lake Erie, nothing but air between us and Canada so when the winter storms come blowing through they really come blowing through. We also store on jack stands, not a cradle. Our club does not have the room to stage boats on cradles or store cradles in the summer. Many members choose to store with their masts up but I can say with 100% accuracy that no boat with the mast down has ever fallen over at our club. On the other hand, several boats with the masts up have blown over in the winter at our club and the marinas all around us. It is also the time that I check the rigging, lights, etc. This winter was an exception, we didn't lose a boat.

Now..........all of that said, each and every time we pull the mast or step the mast it is as Steve said, always very stressful. My wife no longer comes down to the club that day, I call her when we are done. It also requires putting together a team to do it, our club does not have paid help, them members do everything.