I think Anakin should go down Harvey Dent's route. However, i'll make the point after some differences between Star Wars and Rings.
At some point, Anakin's story is the exact opposite to Frodo's story. Lucas set up an order where anakin fell because he was too human. He wanted the jedi order to be morally more than humans, he didn't want them to commit to anybody, nor to help or show compassion, not even to marry.
While the Jedi keep this rigid behaviour, everything develops just fine and the galaxy is in order. But then comes Anakin, who acts like a normal person, chooses his wife over his duty, and so he falls (and the republic falls) because of their forbidden love. Cleary it is wrong for him to be and act just as a common folk would.
Now take LOTR. The ultimate success in Frodo's mission comes from love under the form of pity, because he spared Gollum's life, because Faramir let Frodo go when he wasn't supposed to, etc. In a general way, we are trained (culturally trained) to identify ourselves with characters that show some human scale while heroes are determined, heroes have goals of grandeur and stay on their path. Characters we all emphatise with are the ones that are set in a path that wasn't theirs, and solve things the best they can (Han solo, anyone?)
I'd make a hero of Anakin if I were to make these movies. I wouldn't want anyone to like him but to admire him. Anakin should be incorruptible, the perfect soldier, always proceeding by the book. This blind commitment to civil duty, this inflexibility is what puts him just two steps away from being a monster. He should fall because he denies his human emotions, not because he follows them.
In the end, he falls because the institutions of the republic are rotten. this is the key: The jedi are monsters which is why Luke's Jedi Order wouldn't be just a copy of the preceeding one. You can't prevent humans from being humans, this should be the real tragedy of Anakin Skywalker.
Again: it's the Harvey Dent route, from hero to vilain in two minutes, when he realises he's let so much go and it wasn't worthy. That's the first step to messianism.