7 and 8 are not understood by a lot of fanfic authors, I think. Tamaki has his moments of perceptiveness: such as with the Princess of Monar in Vol. 9. He even has enough of an awareness of sex to have realized what Haruhi's father would have thought when he walked in on them. It's not necessarily that he's too stupid to realize his romantic feelings, he just doesn't overanalyze and subconsciously represses his crush on Haruhi. I think he understands the world fairly well (he DID see through Kyouya after all), he just doesn't spend time moping about it.

Which is why I admire his attitude.

Does 9 mean Kyouya is reborn 20 years later? Not sure what you mean by the last one.