I will be developing apps using both my own Live ID and one specific to my employer. Can I register the same device to both IDs at the same time?
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It wouldn’t be possible at the same time. If you go to the Developer Phone Registration tool you’ll see the message “This phone has already been registered. You can may click ‘Unregister’ if you wish to unregister it.
You could switch the rego between the two though.
With that said, perhaps it doesn’t really matter which live id the device is registered to. After all you can deploy apps developed for either you or your employer regardless of which account it’s registered too.
As a side note, the way the side loading limit of 10 apps is written is this is per device. But it may be worth testing whether switching live id’s offers any benefit.