Without flipping, depending on how a tile is designed (and especially if you are using shadows or beveling) you may need two versions in order for the tiles to seamlessly fit together.
Now, if you're careful about designing them, it's not always necessary. Basically, if you make sure that they're uniformly seamless in every possible direction - e.g., the bevels are the same color - and their bounding box is square, they'll be fine - but, it can be limiting in what you can design. Plus, if everything has to be square, it gets harder to select and move tiles without accidentally grabbing the wrong one, since so much transparent space overlaps.
Having horizontal and vertical flipping is just a very handy tool for the toolbox.
Edit: also, as far as tokens, if you're not using top-down tokens, you might have an image in profile. It just sometimes looks odd for the token not to be facing its opponent.