The first change seems fine from the image. It seems good to not force a minimum size unless truly needed (or something really small), and the default size of the dialog needn't/shouldn't change.

For the other stuff, perhaps it could be made more responsive so that once the dialog gets too small to fit, the contents could start adapting. I think GTK+ 3 has some new widgets to help with this (ex. GtkFlowBox). It would be more complicated code-wise but it would allow your use case without negatively affecting those of us with 4k screens and dual monitors or whatever.

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