I was telling my brother about the recent chapter and fill him on the incoming Naruto talk no jutsu w/ Obito (He only watches the anime ...), and he theorized that it might not be the best idea for him to mention his love for Sakura and compare that to his situation with Rin. He mentioned that decision might end up screwing Naruto over if Obito has a sudden heel turn from being talk no jutsued. As in he looks he's doubting himself, but makes an impulsive stubborn decision at the last minute to prove him wrong by targeting Sakura and putting her in danger as a "You can't possibly understand me if you never went through this" reminder so he could fully test Naruto's willpower. Pretty much like Sasuke's preaching about having never lost his parents the way he did.
I'm mostly thinking no now because it looks like Obito's resolve is completely cracking at this point, but you never know with Kishimoto. I can see him doing that as his last act of stubbornness before getting redeemed.
Any thoughts? How far off base is my brother's theory?