Replace many files with new version at once

Hi,
in WPFD it is possible to replace a PDF (or other file) with a new version - fine.
But once a month I have to replace 50 files of a certain category. Until now I mark the files (one by one) and delete them; after that I upload the new ones and find the right order.
My questions:
1) Is there a much simplier way to do that?
2) How can I mark all files at once (like "Ctrl + a" or ...)? To delete the whole category and create a new one is no option as I use the shortcode on a certain page.
Thanks for your help.
Regards,
Christian