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Turns on immediately with "H9 Max v5.3.0. Now, sometimes when I tried the update there would be an "Update Bad" message. But aside from that it always starts normally.
Alright, that sounds promising. It's a bit mystifying though that you're having trouble updating with USB as well. We do hear from people having trouble updating via Bluetooth fairly often, but they are almost always able to update via USB.
There's an alternative updater bundled into H9 Control called the Eventide Direct Updater. It differs from the updater in H9 Control in that it writes an update directly to where it's supposed to be installed; that means that unlike the H9 Control updater, if it fails while updating, you'll no longer be able to use the H9 b/c it will try to start from an only partially installed software update. So, don't try updating this way if you have any important shows coming up.
When you open H9 Control, if you look at the Mac menu bar at the top of the screen and click on the Window menu, you'll see an option there labelled 'Open Eventide Direct Updater'. This updater only works via USB, and you'll want to start your H9 into Update mode to use it. You do this by turning it off and turning it on again with the HotKnob switch pressed (the switch in the upper left hand corner of the H9). It should be self explanatory to use.