Odysseus is described as more cunning and is seen as a positive trait rather than a liar and negative.

In which Homeric Poem? In the Odyssey he's usually described favorably (although far from always) but in the Iliad he's easily among the least likable of the Greeks. Achilles describes him as:

ἐχθρὸς γάρ μοι κεῖνος ὁμῶς Ἀΐδαο πύλῃσιν/ ὅς χ᾽ ἕτερον μὲν κεύθῃ ἐνὶ φρεσίν, ἄλλο δὲ εἴπῃ.

For hateful as Hades' gate is the man for me who conceals one thing in his heart but speaks another

So there's the most heroic of the heroes saying that he despises Odysseus, who's just tried to use rhetoric and trickery to get Achilles to rejoin the fighting. Odysseus in the Iliad is a hero and does get his chance to shine, but he's hardly the most admirable of the bunch. Odysseus bears a number of impressive traits in the Iliad--he's extremely brave, despite not being especially powerful (for a champion--of course, compared to a regular guy...), he's the best advisor, he's devoted to helping Agamemnon--but his craftiness in particularly is not always seen positively. Odysseus lies and breaks promises--in addition to what Achilles says about him, there's the famous incident in the Doloneia when Odysseus evades Dolon's request to be ransomed, changing the subject without really answering, and has Diomedes kill him out of hand after they get the information they want out of him. Odysseus also tricks Ajax during their wrestling match, foreshadowing Ajax's eventual suicide after Odysseus uses his craftiness to win the armor of Achilles--this was a favorite subject in tragedy, where Odysseus was rarely portrayed particularly favorably. In Roman verse, particularly the Aeneid, Ulysses is a tricky little bastard who can't be trusted. The favorable portrayal of Odysseus is hardly consistent, even in Homer.

Anyway, we've got lots of reasons to believe that lying was bad. The Trojans are oath-breakers, it's one of the reasons why their city is doomed to be destroyed, since Zeus is no longer willing to protect them. Plato doesn't go so far as to say that rhetoricians lie, but he says that they bend the truth and make things seem the way they want people to see them, for which he condemns them. Herodotus has Cambyses put Egyptians to death for lying. In Roman literature lying is never a good thing, and telling half-truths is something that Greek sophists do.

If you can maneuver around someone with speech alone regardless of the truthfulness to it is it seen as a positive? How widespread is this belief?

The debate between "Right" and "Wrong" in Aristophanes's Clouds is at least tangential to this -- it is less about truth and lies per se, but it is certainly about using speech to circumlocute justice. "Wrong" wants to teach Pheidippides to use clever speech to avoid having to live a just life; "Right" wants him to be old-fashioned and proper. Aristophanes has the two engage in a debate, and of course Wrong, being the more clever of the two in argument, wins, but it's clear that this is a social commentary and a joke (his clinching argument is that Right is doomed to lose, since he gestures to their judges, the audience, and points out that they all have loose sphincters, and are therefore on his side), rather than an endorsement. Much of the idea behind the play is a reaction to the worry that sophistry was in some manner undermining honesty in contemporary culture.