4. Pledging stock to borrow against it
Does not transferEllison’s play needs a liquid listed security, a private bank willing to lend against it, and enough scale that the loan is cheaper than the tax on a sale. You have none of the three. Pledging shares in a private Ontario corporation does not produce a securities-backed line; what it produces is a personal guarantee on an operating-company credit facility, which moves risk toward you rather than away, and is the opposite trade.
One point worth carrying across anyway: in Canada, interest deductibility under paragraph 20(1)(c) turns on the purpose of the borrowing, not on what secures it. Borrowing to earn income from a business or property can produce deductible interest; borrowing against the same collateral for personal consumption does not. Collateral is not the test.