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We have a traditional stuffing box on our boat and I have never worried about winterizing the cutlass bearing (exit point of prop shaft on hull). As others have said, water gets in and acts as a lubricant when in the water. Once the boat is pulled out most of the water drains out due to gravity leaving only a small amount as our shaft is pitched down and aft. Air can get in around the small interstices of the cutlass bearing and the shaft and there is plenty of room for ice to expand (we are probably due for a new cutlass bearing).
If you have the PSS dripless shaft gizmo you might be able to sneak a little pink RV anti-freeze in there. Most people seem to have more pressing winterization issues to deal with as there are many, but this is not a big one IMHO.
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"The cure for anything is salt water~ sweat, tears, or the sea." ~Isak Denesen
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