Love this idea. I'm a Red Sox collector myself and I'm always thinking of my top ten. My list would be similar but I do think Lester might be a stretch for a top 10 Red Sox for me over Lynn or Fisk. Here might be an idea for Pedro if you decide to go with an auto if you could track one down . I got this one out of a box break and its one of my favorite cards now.
Good luck with your quest!