SAO. The game had a world wide release and all the countries were trapped in the game with their people. Also it'd be interesting to see modern versions of the characters, I think most/all of ヘタリア takes place over years 30 ago, but the world's changed quite a bit recently.
Hard choice, although it would be slightly interesting if it was crossed over with naruto, well it would also be kind of sad, because there would be alot of deaths. :/
Pokemon!!! Corny, I know but, gosh I 愛 Pokemon and ヘタリア crossovers so much! My most favourite childhood アニメ crossed over with my most favourite アニメ would just put a huge smile on my face! I would 愛 it so much! <3