You can edit your keyboard shortcuts (Edit > Keyboard Shortcuts) to assign keys to the Image Rotation menu item.
When you're in the Keyboard Shortcuts window, select Application Menus from the Shortcuts For dropdown. Then expand Image >, scroll down until you find Image Rotation, then assign your shortcut of choice.
Howard, thanks for the pointer on configuring keyboard shortcuts.
I think my point about the crop box user interface is still valid: There should be a simple, quick way to rotate the image in 90-degree chunks.
Perhaps keep the rotation icon, but make it multifunctional: By itself, the icon rotates the image; add the SHIFT or CONTROL key to rotate the crop box.
I can see where the behavior can be a bit awkward. I took moment to play with your steps in the first post. This may help.
When you activate the Crop Tool, rotate the image using the method you posted (start rotating then hold Shift). Once the image is in a portrait orientation, press the X key on your keyboard to rotate the Crop box. Press Return/Enter to accept. That will rotate the crop to landscape as well, and fill the image.
It might help a touch, but I agree, it's slightly awkward, especially with the 'rotate first, then hold shift' step.
Just a side note...
So many digital imaging systems now set an orientation flag in the images... Can we assume you're scanning images from film or something? Why aren't you getting correctly-oriented images in the first place? Just curious. Maybe if that were made better this would be a non-problem for you.
Howard, thanks for the tip about the X key; didn't realize it worked that way when the crop tool is active. But in this case I had set the crop box dimenions, so the crop box starts out with the correct orientation. Having played with this for a day, I conclude that the best approach for this task is to restore the old keyboard conventions for image rotation and rotate the image before launching the crop tool.
I stand by my observation that the rotate key should affect the image, not the crop box because that is consistent with the new cropping paradigm: We rotate the image, not the crop box. I realize making a change this late in the development cycle is awkward -- but if CS6 ships with this behavior, it will become even harder to change later -- and the user interface should be as consistent as possible.
Noel, you are correct: The images are coming from scanned film. All frames get scanned with the same orientation. I want to avoid the "Patient: Doctor, it hurts when I do this. Doctor: Then don't do that!" scenario. Granted: If images are "correctly" oriented, this issue doesn't arise. But not all images are oriented correctly and CS6 should be at least as graceful in handling the task as previous versions.