Ingwe, You could drive to Calgary and fly KLM through Amsterdam to Joburg. Travel time is about 22.5 hours including the 2.5 hr layover in Amsterdam. The permit system for the Netherlands is easy.
I don't think there will be a direct flight to Windhoek for a long time as there just isn't the volume of travellers to warrant it. Also the collapse of Air Namibia and South African Airways has done away with the most likely airlines to provide a direct flight.
Then there is Covid. I flew from Calgary to Las Vegas for the SCI Convention. Both Westjet and Air Canada flights were well below full. Closer to 50% capacity. Air travel has still not recovered from the pandemic.
