Itachi used Tsukuyomi on Kakashi, but was surprised that Kakashi not only remained standing afterwards but that he knew they and Akatsuki were seeking the Nine Tails. Itachi instructed Kisame to capture Kakashi to find out what else he knew and kill the others, but Kisame is parried by Might Guy. With things escalating, Itachi and Kisame decided to withdraw.
I've always wondered why Itachi went to this extent, he brutally tortured Kakashi who was his senior at some point in the past, he was readily going to kill Asuma ,who happens to be the son of the hokage who is protecting the only person that matters to him, and Kurenai.
This is of course out of belief that Itachi is good at heart which was confirmed multiple times.
My questions are:
1. Why did Itachi torture Kakashi this way?
2. Why did he want Kisame to kill Asuma and Kurenai?
3. If Might Guy didn't show up, would he have killed Kakashi?