The New SkullMan is already going to happen. Medicom has already implied it's in the works. It would be cool if it came with 2 Human heads Live action and Anime. The Live Action could be another likeness of Hosokawa as he appeared in Prologue of Darkness.
As for Shippuden, I think Naruto first series and Shippuden are for the same audience, I guess Shippuden is more adult in the sense that the characters are all 2 yrs older but the maturity of the story has not changed much at all it's still very much the same story only the characters are a little older. After all you've been through so much with these characters in the first series that it would be a crime if you didn't see the first series first (Minus fillers anyway) What's more important is that I think Bandai treats Naruto as an age group younger than Bleach as Bleach has a setting that is more marketable towards 16 and up but hopefully that will change with Shippuden since the characters are technically the same age as characters in Bleach.