You can't use one Roku account in two different regions without problems, so your TV in NY should be linked to a Roku account created in the US, the one in Canada should be linked to a Roku account created in Canada, and the traveling stick, well... there's no good solution for a device that travels from one region to another. You either have to factory reset it each time you go from one region to the other so you can link it to the appropriate Roku account or get a separate device for traveling in each region that's linked to the appropriate Roku account.
Note that subscriptions taken out through Roku are linked to the Roku account, so it's best to subscribe directly with providers unless you want to take out multiple subscriptions for the same service.
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