I wondered twenty-some years ago why they didn't just go back to Tatooine with Coruscant pocket change and buy Shmi's freedom and set her up with a pleasant little retirement cottage or a condo in a senior-friendly complex in that Dinotopia-ripoff capitol city on Naboo. Yeah, yeah, Jedi code against attachments or whatever—but it's not an "attachment" if she's just not a slave anymore and living somewhere else that is not misery desert.
Anakin's massacre of the Tusken raiders is also the wrong kind of step into evil, from a character perspective. We're supposed to see Anakin becoming Darth Vader, and Vader is in the main a cold-blooded villain: implacable, determined, even a bit grusomely sardonic. ("Apology accepted, Captain Needa.") An explosion of blind rage doesn't fit. Anakin should have been a cop using excessive force, like maybe killing the alien who attempted to assassinate Amidala while trying to Jack Bauer information out of them.