Bounding Boxes align with artwork

As it is now, when I rotate an entire character, then select an arm for example, the bounding box is not following the shape of the arm, but rather the stage. If I want to squash or stretch something that has been rotate 45 degrees, it now becomes impossible. How do I address this?

The bounding boxes always share the same orientation as the screen. If at any time an item you wish to squash or stretch is at an angle other than aligned with the screen use the Rotate View tool to bring the item in alignment then do your squash or stretch.

But is there a setting to change this? I’d rather it was oriented to the way the drawing or peg was created rather than have to the screen. there must be some sorta preference for this, no?

I am not aware of a setting to change this.

It is subjective but I think this way of doing it is very good, even brilliant. It can be performed second nature like shifting paper to get a better angle for drawing. I really believe that instead of looking to do it another way you should embrace it and give it a chance to see how well it works. The movement can even be done with fingertips with an appropriate track pad or tablet.

You could always temporarily uncheck the 3D Camera option or disable the peg
(select and shortcut d in the network view) - it’s pretty quick to disable/enable.
It really depends on what you need the bounding box for. After stretching the arm you could re-enable the 3D.