Last year, Garmin finally got around to sorta-kinda supporting Mac OS X. I used the version 1.0 of their WebUpdater application for updating the firmware on my portable nav. I bricked my StreetPilot c330.
Another Mac, another portable nav and nearly a year later, Garmin's at version 2.0.1 and an overwhelming majority of the feedback on Version Tracker was positive. My experience, not so much.
The WebUpdater hanged at "Erasing" as the blood drained from my face. After waiting more than an hour, I accepted my perceived fate, disconnected the USB cable and had to wait for the battery to drain on the GPS, as it wouldn't respond to any other input.
Amazingly, after recharging this morning, the thing fired right up and works. No updated software, but it works.
I'm not touching the WebUpdater again. Garmin, I give up.