Help me settle a bet!
This isn''t all that complicated, but you are right that it is easy to see why folks can become confused. A lee shore is always a shore that is downwind so that the wind is blowing onto that shore. It does not matter if a boat is there or not.
The leeward side of an island is to leeward of the island but the shore on the Leeward side of the island would be a windward shore that afforded a vessel a safe lee. Got that? Glad one of us did. 8^)