Canada always will do better at the Winter Olympics than at the Summer Games because winter sports are pursued by far fewer countries. Every nation has a strong track and field program, every region is heavily into the sport. You don't need money to take part in track or soccer or basketball.
Poor countries do it.
Warm countries do it. You do need money to be a skier or a hockey player. Obviously, you also need ice and snow. Canada always will be a hockey power, don't sweat it. Unless, of course, the planet tilts suddenly and a deep freeze settles over the equator.