I consider any use of the internet cheating, moving around isn't - you're supposed to do it!
I find the USA the hardest... I guess it depends where you come from. Europe is easy because even though I don't speak the languages, I can pretty much tell them apart. I can tell if something looks nordic, or german, or french, etc. Japan is small and distinctive so that's good too.
USA... well it all looks the same. Unless you're in a big city, or you're on a road you can find on the little map on geoguesser, it always just seems to be a few houses (with mailboxes! at least you have mailboxes so I know I'm in the US!) and loads of open space. Tell me your secrets! How do I tell once place from another