Can a special assessment be claimed against my rental income? If so, where is it applied? Can unclaimed portions be applied over future tax years?

You can claim the full amount that you paid for the assessment in the tax year.  It will carry forward as a non-capital loss that you can apply against future taxes.  You will likely be required to show receipts for an amount that large.

any idea where that would be in Turbotax

Special assessments of capital expenses should be claimed on the year they are paid. The roof repair cost is a capital expenditure that should be added to the building's depreciable value (class 1). Check these links on special assessment and tax treatment:

https://pocketsense.com/special-assessments-condo-ownership-25723.html

http://www.ourbigfatwallet.com/how-condo-special-assessments-are-treated-for-taxes/

Thank you

Heba

still have no idea what line I would put the assessment on

Thank you for choosing TurboTax.  Depending on the nature of the expense will determine how the transaction is 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.

Therefore, we are not able to provide a specific line to address your question. I am recommending you consult with one of our tax experts who will guide you on the matter.

 Please use the link below to access their services:

https://turbotax.intuit.ca/personal-tax-software/live-catalogue.jsp