When a browser vendor implements a new css feature, it should support it, from day 1, both prefixed and unprefixed, the two being aliased. If a style sheet contains both prefixed and unprefixed, the last one wins, according to the cascade.
Authors should write their style sheets using the unprefixed property, and only add a prefixed version of the property (below the unprefixed one) if they discover a bug or inconsistency that they need to work around in a particular browser.
If a large amount of content accumulates using the a particular vendor prefix to work around an issue with the early implementation in that browser, the vendor could decide to freeze the behavior of the prefixed property while continuing to improve the unprefixed one.
Makes sense, but still the problem will exist that many examples that exist now only contain a prefixed version (those “Webkit only”-demos) of a property, breaking in other browsers — hence Opera about to support -webkit prefixes.