My picture goes something like this. *Locally* the codimension 1 skeleton is two-sided, so while you're attaching, you have to traverse it twice to "attach both sides". If you always traverse in opposite directions, you get the 0 map in homology and have orientability.
In the other case, you traverse it twice in the same direction (so in homology you get a multiple of two, which is consistent with cellular homology), but have "flipped sides". In a surface, this corresponds to an embedded Möbius strip, but in higher dimensions I have no imagination.