Does Cortana's upgrades rely on the OS for upgrades or can it be done via a laptop or something? on

Cortana is almost entirely cloud based so updates are dynamic therefore that are done by Microsoft and the changes then rollout to users. The stored data which is the information you have let her access + keep in her notebook, are saved on your phone. However your Bing data is stored in the cloud and syncs between devices, you can delete this via Settings -> Applications -> Cortana -> Delete Cloud data
 

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