Hi,
Currently, this is not possible to do via the User Interface or REST API. So, it would require custom code on both the backend and frontend to support linking a Bitstream to multiple Items. This is not an easy task unfortunately. You'd likely need to add a new REST endpoint to link bitstreams into multiple bundles, similar to these:
https://github.com/DSpace/RestContract/blob/main/bitstreams.md#bundle Then you'd have to create a new interface/page which could call that endpoint. I cannot provide any more specific advice than that, as it's not simple.
Tim