A senior agent from CRA finally called me and was able to answer my question so here it is.
What can we claim in terms of training expenses?
Any training you take that gives you a lasting benefit (e.g. a new skill) is considered an eligible capital expenditure and is claimed similarly to how you would claim capital cost items (an allowance each year that you write off annually until the balance is 0). Any training that maintains or upgrades your current skill is considered a current expense and can be written off 100% in the year you incur it. So, the initial First Aid/CPR training you take is an eligible capital expenditure because it is a new skill you're learning, and any renewal courses you take after that would be a current expense.

































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