Transparently, it might be better to upload the files you’d like to share to a platform like Google Drive, Box, DropBox, OneDrive or others, and then post the file link in the Updates section directly by using the option within the UI. I think that would be a better solution in this case specifically.
That said, I do think this aspect of the platform could be better - I’ve gone ahead and passed your question as feedback to the development team
Last, but not least - I’ve noticed this post didn’t seem to have a Sub-Category, and that’s totally cool. I’ve already added one on my end. It would really help if we could keep mindful of the categories within the community though, as that helps keeping things tidy and easy to find. I hope that makes sense.