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The two proposals are quite different. Siciliote Greek, as deduced from latin loans, is a generic Doric Greece, for which Syracuse's founder Corinth could serve as a model, while Masaliote Greek is derived from the Ionic of Phocaea in Asia Minor. Both, however, were extremely early foundations from their mother cities. Any Romanceoid development, however, would occur after Hellenistic influence and the spread of Koine to both place (especially Sicily, which always attracted new mercenaries and settlers). A timeframe before the loss of quantity and multiplicity of [i] in Greek would be ideal; in that way, the distincitions between [e] and [E:] and [o] and [O:] could be used to enhance the Romance quality. Diphthongs, of which Greek has many, could be a problem. Would you want the aspirates [p_h] to become fricatives [f]?