Revcan has suffered a few groundings as it has attempted to navigate its way to the treasure islands known as the taxpayer pocket. Where there used to be a clear channel of disallowing the taxpayer to, as the House of Lords said in 1938 "to arrange his affairs in such a manner as to attract the least amount of tax", this has now been blocked. In the old days if you mortgaged a business asset to pay off a personal indebtedness, Revcan would disallow the interest expense on the the new higher business indebtedness. An Edmonton lawyer by the name of Singleton sold his interest in his legal practice to his partners for $300,000. He then applied the proceeds to cover his mortgage (for which the interest was non-deductible for tax purposes). That same day he went to the bank and took out a loan of $300,000 and used the proceeds to buy an interest from his ex-partners in their legal practice. The interest on this $300,000 loan, according to Singleton, was a tax deductible expense because it was money borrowed to buy an income producing asset. Not so said Revcan, section 245 of the Income Tax Act clearly states that when a commercial undertaking is solely for the purpose of avoiding tax, the Department has the right to overturn it.

Singleton fought it all the way to the Supreme Court of Canada and won. So now any Canadian with a business asset can dispose of it, apply the proceeds to his personal indebtedness and borrow to finance the business asset.