Special assessments of capital expenses should be claimed on the year they are paid i.e. 2021. You can provide the cheque payment proof if required by CRA. However, it is more important to understand the nature of the expenses whether they are required to be capitalized or expensed. For details on that please check this link How Condo Special Assessments are Treated for Taxes
Depending on the nature of the expense will determine how the transaction needs to be treated. Expenses that bring the property back to its original condition can be expensed within the tax year. On the other hand, expenses that improve the property beyond its original state and improve its value should be claimed over several tax periods.
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