Hi Jonah - that would definitely be good from a UI space standpoint, but that set of "draw" tools are focused on drawing an object from scratch, not really on processing a selected object.

I was thinking that a "create bounding box" type function might fit in best as some kind of option right in the bounding box properties panel instead...

One nice thing about having the bounding box as an editable object property is that it should remove the need for creating the box as a separate object for some of the things you were describing, like quickly checking measurements and resizing objects.

- Michael