@Multichill has figured out a nice workflow / method to directly upload images to Wikimedia Commons based on Wikidata items, using the Commons compatible image available at URL Wikidata property. See https://commons.wikimedia.org/wiki/Special:ListFiles/BotMultichillT
If reliable enough (i.e. @Multichill's bot operates relatively autonomously and does not need his personal intervention/activation/reboot for most of the time), it's a good idea to document the exact conditions under which this process will work, so that it can become an actually quite easy upload workflow (including StructuredDataOnCommons) that can be used by many partners and community members.
@SandraF_WMF will then include this documentation in the general SDC-GLAM documentation portal.