My Luck

Yes. Newmarket. Although they just bought a house in Barrie on Lake Simcoe. They will be moving in about a month.
Thought so. At least you'll have a straight run up the 400 although that can be a crazy highway at times.
I prefer to go across country now. It takes an extra 30 minutes but safer than the 400 series hwy. Going through Brampton you might take your life in your hands haha. (AKA Bramladesh)