1. Closest point of land is Port Aux Basques. A fine spot it is.
2. There must be 100's...at least. Many abandoned communities as well.
3. St Pierre is an interesting curiosity of French territory. Best Croissants et patisseries ever!
Also, their alcohol is not taxed...so...plan on stocking up if you go.
4. You can't go wrong with either option. Pay particular attention to the
weather if heading over to the Rock. It gets nasty. Louisburg on the south coast of Ile Royale (AKA Cape Breton) is a federally funded re-creation of coastal life in the mid 18th century. It is well done.
Google it. The "Capers" say they're really Newfs who ran out of
money on the way to Toronto! Truly excellent people in both places.
Full disclosure: I'm a newb sailor originally from Newfoundland and I've been to all the places you're asking about. My vocation is airline pilot. PM me if you like.