I'm surprised they made an EPII Obi Wan before an EPII Anakin. And so soon after the Clone Wars Obi Wan. You'd think they would have made every Vader and Anakin by now, since Lucas considers him to be the main character.
Well, I think Ep II Obi-Wan is a result of the sculpt being ready from Clone Obi-Wan, I imagine if the Clone figure hadn't come out, we may not be seeing this one right now.
As for character choices, could be wrong, but I believe Sideshow has free reign over what things they want to do and just presents them to LFL and gets a greenlight or red light on the project, I don't think LFL says you guys need to make ________ now.