CRA accepts that “in contemplation of” can be backwards looking
After quoting from Copthorne as to the meaning of the extension in s. 248(10) of the concept of a series of transactions, CRA stated (in the context of a question on s. 55(2)):
Therefore … “in contemplation” is not read in the sense of actual knowledge, but in the broader sense of “because of” or “in relation to” the series. Therefore, this can be applied to events either before, or after a specific transaction.
Therefore, the sole factor of transactions occurring at the same time is not necessarily a deciding factor either way. The transactions are reviewed in the context of the transaction identified and used to apply to the specific section of the act, in this case subsection 55(2).
Neal Armstrong. Summary of May 2019 CPA Alberta CRA Roundtable, ITA Session – Q.7 under ITA s. 248(10).