I think everyone has a problem with borders that involve an idiot with a ruler that has no idea what's going on at the region of which he is drawing the borders. For when they kinda sorta work and still look butt ugly, see American States. For when they work for jack shit, cause more problems than they solve, and also look ugly, see Africa and Middle East.
If your border cuts a town in a way that makes some poor schmuck require a passport to go to the kitchen, you are doing something wrong.
To be fair, straight borders isn't as much of a problem in North America when most of them aren't national borders, save one really, really long one. That said, sucks to be the odd US town which was missed and thus need a passport to pass through Canada to get to the mainland. Or Alaska.