I want to do a Free Transform - Scale on something but I don't want to scale it by stretching it straight up vertically or straight across horizontally - is there a way to rotate the bounding box first and then scale the item?
For example lets say you painted someone laying down with their head on a pillow (at an angle) and then later you realized that you want to stretch their face vertically a little to adjust their facial proportions without repainting - the problem is that their face is not vertical in the image but diagonal -so I need to rotate the bounding box before Scaling.
Keep in mind I know that I can rotate a selection by using Select - Transform Selection but that is different than actually rotating the bounding box of a Transform BEFORE Scaling.
No the bounding box is always parallel to the edges of the canvas. I wish it had that feature also. For now you stuck with the procedure that you mentioned.
I'm not on a computer with PS so I can't try. But what if you first rotate the canvas (I mean just the image view), which came available in CS5, and then use the transform? I've sometimes hoped this, too, but never actually tried this way.
Well here is the only way I know that can work. Select and copy the area onto a new layer. Transform the selection to be straight up and down...like a face. Then transform again and you will have your handles where you want them.