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I'd recommend storing the mast horizontally
I can confirm that leaving the mast vertical is a bad idea. I had to get the mini-sledge out to close the sail track on a H16 mast after water froze up and pushed the track out.
I have seen boats in varying states of terrible condition, and the obvious damage always came from something significant. Soft spots from hard impacts, holes from sharp impacts, excessive beaching wear. I don't know that I have ever seen any bad damage from out of the water winter storage.
So, basically, don't worry. Make sure the hulls can't fill with water. If you feel like it, take off the rudders, tramp and the running rigging. They will last a lot longer...
Don't pull the drain plugs unless the boat is tilted way back to drain, or the hulls are covered with a tarp. I have found in the summer months if my drain plugs are pulled my hulls take on rain water as in runs down the transom and into the unplugged drain.
Same logic for the port covers.
I will be winterizing my boats today... I live in Northern lower Michigan. I suspect most people got around to it a little sooner, but I just couldn't let the season go that easily.
-Joe