In past years I have asked the other contributors if they know the answer to that question - without answer. The tax wording does not specify whether the 30 days is between the transaction dates or the settlement dates.
For issues of "which year is the sale reported" it is the settlement date that decides it. For issues of foreign exchange rate used to translate into Loonies it is the transaction date. So take your pick for this issue.
The simple solution is to use the settlement date for the sale and the transaction date for the repurchase, just to be safe. Or just buy a similar security right away. Almost everything has a look-a-like twin.
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