1. I agree with you in that I enjoy the season more than the actual day. I enjoy Christmas Day, put part of the fun is preparing for the big day and the anticipation.
2. Nah. I wouldn't want to extend the season. But I've always including Thanksgiving as a part of the "Season". When I think of "The Holidays", I think of Thanksgiving, Christmas, and New Years. So, for me, The Holiday Season Starts November 1st and I usually step up my fall decorating and sometimes, Christmas sneaks in a little early. But I guess that, in a sense, I have extended the season, but I wouldn't want to start in October. However, if want to start in Octoer in your home then I say GO FOR IT! You're the only one that can say what's "too early" in your own home.
3. I have to say Johnny Mathis. He just sounds like Christmas to me. His rendition of "The Most Wonderful Time of the Year" is my absolute favorite.