I absolutely love this. A rival that's attracted to you is something I've wanted for a while now, and I really like the idea of the two sibling Gym Leaders. The details you've gone into is amazing.
Seeing as you've gone into that much detail, why not mention things like events that happen on the player's birthday, like we get in games at the moment? Your Rival having a weak moment and giving a huge hint towards attraction to the character could be cute.
Wow, you put a lot of effort into this. I really like the idea. Keep up the good work!