In countries beginning with D, I think D.R. Congo should sort by the full name, i.e. Democratic. That's where Countries that Start with D put it, though they made it a more obvious fill-in-the-blank answer.
Lots of fun! I’d definitely argue against using the city proper population of Vancouver for the Canadian cities one. Vancouver is definitely the third most populous Canadian city.
In countries beginning with D, I think D.R. Congo should sort by the full name, i.e. Democratic. That's where Countries that Start with D put it, though they made it a more obvious fill-in-the-blank answer.