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For me, Itachi is a hero, insofar as the nobility of his goal. How he chose to go about achieving that goal can be seen as villainous (as it certainly was), but the goal is what's important, in my eyes.
This is best illustrated in his fight with Sasuke, particularly the end. I suspect that, as soon as he saw Sasuke, Itachi knew that Orochimaru was inside him, looking for an opportunity to get out. My suspicion is that Itachi's thinking was something to the effect of "Well, fuck. I can't do what I came here to do, because I have to kill Orochimaru now." Had that situation not transpired, I suspect Itachi would have been able to convince Sasuke that what he did in the past was a necessary evil to eradicate the far greater evil of the present.
My guess is that Itachi knew that he could not defeat Madara, but saw that ability in Sasuke. He had planned to try and explain that to Sasuke, but was unable to do so because of the whole Orochimaru situation. As it stands now, we know that Sasuke has, essentially, become Madara's pupil, which I consider to be precisely the opposite effect Itachi intended.
Brutal though his tactics were, I think that his end-game had the best intentions in mind. While I realize "the road to hell is paved with good intentions," I respect Itachi's attempt to quell this evil through the means he thought most appropriate, and consider it unfortunate circumstance that his plans could not fully come to fruition.
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