I seen the flashback as showing Rin as someone that supported his dreams. At this time he was looked down at by Kakashi far as his skills and dedication.
I didn't see Rin flirting with him and Kkashi thru all the flashbacks. I saw Obito crushing on her and Rin admiring both. Kakashi for his skill and Obito for his heart. I mean has he ever said he was in love with Rin,now? So far his actions up until the Madara encounter, mimicked Naruto.
I'm just saying that Obito was a goofy kind hearted kid that became a crazed man. But,deep down he wants a reason to go back to the way he used to be.
All that said, I personally want him to slap Naruto's hand away. Them force Naruto to have to take him down. Probably not gonna happen.though,only true villian here is Madara and he will probably end up killing Obito himself.