nuvi 14xx root should be like this one:
ouFpt

Code:
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Bring nuvi12xx_13xx_14xxKeyboards_320.rgn to computer where your device is attached.
Then you can drag-and-drop nuvi12xx_13xx_14xxKeyboards_320.rgn onto the WebUpdater icon on your desktop.

Try to clean Vehicle folder, backup first your files on Mac and run again Webupdater or Express.