Can restructuring my corporate group right before a sale be seen by the CRA as abusive tax avoidance?

Yes, this is a real risk, particularly where the restructuring's main apparent purpose is reducing tax on a sale that's already substantially arranged, rather than serving any independent business purpose. The Income Tax Act includes a general anti-avoidance rule allowing the CRA to deny a tax benefit obtained through a transaction, or series of transactions, that technically follows the letter of the relevant provisions but is found to abuse their underlying purpose. Restructuring aimed at accessing or multiplying the capital gains exemption, or converting what would otherwise be taxed as a dividend into a capital gain, timed right around a sale process, is exactly the kind of pattern that draws this scrutiny.

This doesn't mean all pre-sale restructuring is abusive. Genuine succession planning, estate freezes, or reorganizations done well in advance of any sale process, for real business reasons unrelated to a specific pending deal, are common and generally accepted. What tends to matter is timing, whether there's a genuine business purpose beyond tax reduction, and whether the structure reflects real economic substance rather than existing purely on paper.

Because this determination is highly fact-specific, get a tax advisor's assessment before implementing any restructuring close in time to a sale process.