What's Horrace doing off of the Island?

I was recently watching season 3 and the episode The Man Behind the Curtain, and I caught something that has me thinking now. When Ben was born, Roger brought him and his dying wife out to the road or interstate where we see Horrace and some lady with him pull over and help Roger. Then, later on in that episode, Roger says Horrace was the one who helped get him the job when Horrace introduces them to the island. So I began to wonder if Horrace wasn't a member of the DI when he found Roger and baby Ben that day. He must have come to the island between the 12 years before Ben arrived on the island. This also has me asking two questions as well. How did Horrace come to be the leader of the DI, and who on earth is the lady in the car whent they found Roger? Did she go on the island as well, or did she stay behind? Horrace sure did grow out his hair pretty long on the island too. :) :) :) Any thoughts?

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