The reason adding custom roles works on after_switch_theme is because roles are saved in the database. In fact, because it saves to the database, it should not run on after_setup_theme.
add_image_size(), on the other hand, does not save anything to the database, so needs to run on every page load, and needs to be hooked on a hook that runs for every page load. So after_setup_theme is the correct hook to use.
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