2) that's not Ken Caillat but Benmont Tench, a founding member of Tom Petty and The Heartbreakers. He played on Stevie's records and toured with her in the 80's. This pic seems to have been taken during the Wild Heart tour, 1983.
4) I don't know at what event this photo was taken but I do know Stevie uses this photo in the Landslide slideshow during her solo concerts, you can see the photo at 1:46 in this video:
http://www.youtube.com/watch?v=tzsf72lYLo0