Can I duplicate an item via automation to a separate board and bring files with it?

@Sven.H

Have you looked into 3rd party integration software yet? I use Integromat and you can run the automation through that, have it download the file and re-upload to the newly created item. The FREE plan is generous enough to test and see if you like it with no time restrictions. The obvious downside is that if you are using more than the FREE plans actions/data then you would need to upgrade but the first tier gives a 10x upgrade for a reasonable price.