Okay, I'll take a shot at these:
1. Meredith
2. Nevada (Las Vegas)
3. Another Great Lakes ore carrier that was on Lake Superior the night the Edmund Fitzgerald sank. The Anderson responded to the Fitz' distress calls but arrived too late.
4. Dream Street Rose
5. Bill Lee (Spike Lee's father) played stand-up acoustic bass on Lightfoot's debut album.
5.(#2) John Sebastian wrote the theme song for "Welcome Back Kotter." He was the lead singer/songwriter for the "Lovin' Spoonful."
6. Sit Down Young Stranger (IYCRMM). Sebastian played harmonica and autoharp on this album.
7. Cold on the Shoulder shows a woman standing in the background.
8. Couchiching.
9. Drink Yer Glasses Empty.
10. ? I have no idea!
I'm guessing on a few of these. Please let me know how I did!