Your Obito/Madara was actually pretty interesting (and thought out).
As for the interrogation thing it could go a few ways I guess:
1.Tsukuyomi or a varient was used to torture it out of him (Cruciatus curse

)
2. Sasuke was training with the Jedi

(but seriously he might have some form of persuasive power)
3.He can read minds or something similar.
I haven't really been paying the closest attention to things though, I may be totally wrong.