Is it possible to update an ATV2 running 4.4.3 to a firmware version that can be jailbroken without tethering, say 4.4.4 or 5.0.x?
I imagined I could just download the 4.4.4 restore IPSW from a source like this and then option-restore it in iTunes, but apparently iTunes objects to restoring to any firmware that I want?
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You cannot upgrade to a version of firmware that Apple is no longer signing unless you already have ssh blobs for your device with the target release. In your case I assume you have no saved blobs for 4.4.4 so that currently limits you to the 5.0.2 firmware version if you want to be able jailbreak as that is still being signed by Apple (although we do not know for how much longer).