One interesting thing about JPEG is that you can rotate an image with no quality loss. You don't need to convert each 8x8 square to pixels, rotate and convert back, instead you can transform them in the encoded form. So, rotating each 8x8 square is easy, and then rotating the image is just re-ordering the rotated squares.
I'm not sure if this is how JPEG implements it, but in H.264, you just have metadata which specifies a crop (since H.264 also encodes in blocks). From some quick Googling, it seems like JPEG also has EXIF data for cropping, so if that's the mechanism that's used to crop off the bottom and right portions today, there's no reason it couldn't also be used to crop off the top and left portions when losslessly rotating an image's blocks.
Indeed. Whenever I'm using an image browser/manager application that supports rotating images, I wonder if it's doing JPEG rotation properly (as you describe) or just flipping the dumb flag.