Hello! You should turn on gl_drawable_resolution to fix this - it's an argument you can pass to the outline_transform transform via drawable_res=True.
Viewing post in Cropped imageBlurry
You need to use mesh padding or increase the transparency around your image to accommodate the outlines, yes. Mesh padding will change the size of the image, so I recommend padding the image with transparency outside of the engine.
You'll always have at least a small quality change when resizing images in Ren'Py also, which isn't under my control/it will look like that regardless of the outline being applied if you've toggled the drawable resolution property on.