How aggressive is WS with respect to carry-on bag size, and do they give any slack for Gold status members (received through a status match)?

I have a YEG-OGG flight coming up with the family. Would probably have gone with AC if service from YEG was non-stop and non-rouge, but the direct flight was too enticing. We'll have plenty of free checked luggage allowance available, but I am wanting to bring along my B&R roller which is 22" rather than the 21" officially allowed by WS. I've never had trouble with it on AC and I think my SE tag keeps the GA's from asking for measurements. I don't overstuff it, but will have items that I don't want to check underneath the plane. I could take multiple smaller bags, but prefer keeping everything together in a single unit to ease passage through the airport. Any recent experience on this front?