Apparently you missed the "almost", no prize for you.
Your words were "It makes it almost certain that..."--how does the "almost" change the fact that you took a slightly plausible notion (Sakura joining Ino and Chouji to retake the chuunin exam) and ran with it as though it were "certain"? Just because Sakura and Ino are friends does not automatically mean they joined up to retake the exam; assuming they did and claiming what you believe could have happened next is "almost certain" does not make it so. No prize for you.
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That being said everything I said fits perfectly well with the characters development in canon. the only real guess is about Sakura being the third on Team 10's second try and that's no real leap either- hmm, they need three to enter the exams, Shikamaru is already a Jonin so Team 10 is short one person. Team 7 is now just one Genin, the other teams aren't missing anyone so, you know it's a pretty freaking obvious thing to figure out.
Not entirely obvious, no. Hmmm, Sakura needs to pass the exam and would most likely, being the smart girl she is, look for a team she could fit in well with. Considering Ino and Chouji rely on someone that can hold enemies down for their combined attacks to work, Sakura wouldn't be a likely candidate. I'd almost guess Sakura would look for a group with more leveled abilities in taijutsu, but that's beside the point. Point is, it's not "pretty freaking obvious" that she'd join up with Ino and Chouji. Possible, but not the only way things could have happened.
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Tsunade's behavior in chapter 248 around Sakura showed an obvious awareness that Sakura had been missing and had become attracted to Naruto, and Sakura's overt flirtation with Naruto again makes this another pretty freaking obvious thing to figure out.
248? The chapter focused mostly on Gaara and Deidara fighting? I'm going to assume you mean 245, when Naruto comes home. If that is the chapter you mean, I'm strugglin' to find any evidence that Tsunade was "obviously aware" of Sakura's attraction to Naruto. Aware that she missed him? Sure, that'd be a given, but here's all of Tsunade's interaction with or around Sakura during that chapter:
--tells Sakura that Naruto's come home-->no nudgenudge-winkwink add-ons to imply that Tsunade thinks there's any *special* reason Sakura might want to know Naruto's back
--talks to Jiraiya about how Naruto's become more like him-->nothing implied there except that she doesn't like seeing Naruto become a perv
--tells the group to cut the "emotional reunion" short-->honestly, from the look on her face I'd say she was being sarcastic when calling it an emotional reunion
No "obvious awareness" there to me. As for Sakura's flirtation, it's minute. I've seen you consistently imply that Sakura was "overtly inviting Naruto to view her body in a sexual way" (read it so many times, I know the exact words), and honestly? I think you're full of it. Yes, she was flirting, and yes she asked him whether she'd become more womanly--but that doesn't mean she was being overtly sexual or making invitations to jump her bones. There's no way for me to deny that she was flirting with him about her appearance which implies some level of physical/sexual attraction, but I find it hard to believe that not even five minutes after seeing him for the first time in two years, she was trying to go sexual all over him.
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Sakura was already showing a conscious letting go of her romantic feelings for Sasuke, and her affections drawing toward Naruto when she interacts with him in the hospital at the end of part 1. Note the very marked lack of romantic actions even when Sakura sees Sasuke for the first time in two and half years, much less when she attempts to fool him that she wanted to join up with him. She couldn't even fake a fangirlish reaction. If Sakura has romantic feelings she's really obvious about it. If you pay attention to the hospital scene with Naruto at the end of Part 1 thoughts of Sasuke make her depressed, but thoughts of Naruto have her acting as her true self- smiling and determined. Asuma was much more observant of people's feelings than Kakashi is. It's pretty obvious what Asuma meant. What did you think Asuma meant? That Ino should keep fighting Sakura for Sasuke's affections when Sasuke, even in part 1 had no interest in either, and frankly, if anything loathed Ino even more? Then on top of that Sasuke was even then known to willingly be with Orochimaru, to the point of attempting to kill his team mates for just wanting to talk to him and beg him to come back to Konoha.
Her affections drawing towards Naruto in the hospital--debatable. When I read that scene, it appears more to me like she's working on getting past the pain Sasuke's inflicted while letting Naruto know that she's there for him; she's working on being a friend and teammate, not acting on her suddenly realized romantic feelings for Naruto. Of course thinking of Sasuke's going to make her depressed; the guy just ditched them all for a creeper with power, knocked her out and left her on a bench,
and beat the snot out of Naruto. And of course thoughts of Naruto are going to make her more smiley and determined, that was a side-point of the PoaL: to make Sakura realize that Naruto not only understands her but is also capable of supporting her with his determination. Touching and strong foundations for their later relationship: yes. Proof that at that time Sakura was romantically inclined towards Naruto: no.
What the hell kind of romantic reaction would you expect Sakura to show when they finally met up with Sasuke? Even if she still had feelings for him when they found him, he was still the guy that had torn her world down when he left; it'd be like meeting up with the guy that you want to cure of cancer despite him dumping you. At the same time, though, just because she didn't flush or flash sparkling shoujo eyes at him doesn't immediately say she was over him.
As for Asuma, let me start off by saying I really couldn't care less about who Ino ends up with. Love the girl, but don't strive to determine whether or not she'll end up in a pairing. That said, I don't think Asuma had any particular boy in mind when he told Ino not to lose to Sakura in love. These were his dying words to her; don't you think if he had really had a guy in mind that he thought Ino would be happy with, he would have at least said the guy's name? Given that he didn't, we're left to assume that he said it only because he knew she and Sakura would always have some rivalry between them, and that Ino should never settle for anything; she should make sure to find someone amazing. And also given that Ino's a minor character whose love-life has no impact on the plot, Kishimoto wouldn't have been ruining anything by tossing in a guy's name there; since he didn't, I don't think Asuma's words were meant to be related to Sasuke, Chouji, or anyone else you can think up.
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Clearly Asuma had seen Ino and Sakura interacting since the first Chunnin exams, and noticed how Sakura was not just becoming more skilled and powerful, but emotional she was leaving behind her childish one sided crush on Sasuke. Asuma was worried Ino hadn't grown up and seen reality and knew he could spur her into action by invoking it as a challenge to outdo Sakura.
And you know, denying Sakura's change in her feelings would be like saying Kushina never changed her first impression of Minato. Kishimoto made the parallel overt.
Now I'm confused. You've said that Asuma had picked up on Ino having romantic feelings for Chouji, yet say here that Asuma was worried she hadn't faced the reality about Sasuke and used his dying words to tell her to grow the hell up? How ass-backwards.
Who's denying the change in Sakura's feelings? If you're implying that I have, then be assured I have no doubt about them. (Would be kind of silly for me to be on this site if I did, right?) If that comment isn't directed at me, then you have me all the more confused.