Selection relative to current rotation
It would be nice if selection bounding-box and stretching would be relative to current rotation angle.
I'll be honest, I'm not sure what you mean here. Could you maybe show some screenshots? Or is this already implemented and I'm just forgetting here...?
Well, when stretching a selection, it is transformed as a rectangle. When rotating the selection and then stretching it, it is transformed as a rhombus, therefore skewed.
The idea is that even with rotation applied to selection, it is still transformed as a rectangle, preventing skewing. Photoshop's selections work like this. So, basically, the skewing behaviour is removed from stretching rotated selection, and moved into its own mode.
The benefit is being able to stretch a selection without skewing, even after rotation. The downside is that it doesn't double as a skewing tool.
This is a mockup of the idea.

This is implemented now. It works even when skewing and distorting the transform, so nothing was taken away in that regard.
It's available in the continuous release: https://github.com/drawpile/Drawpile/releases/tag/continuous
Thanks for reporting it!