I have only positive experiences of both countries. But if you all how many people from X will want to visit Y, my guess is that more Canadians visit Namibia then the other way around, by a large factor, and a bit of extra bureaucracy won't be worse than the overnight flight anyway.
Digression alert: an airport security guard in Namibia found a knife that I've carried for almost fifteen years, on countless flights. https://www.spyderco.com/catalog/details/C133/Bug-trade-Stai...