Is there a best way to replace several PDF files?

It's probably worth speaking to the reseller who helped install M-Files.  What you're describing sounds like an overly error-prone and manual process.  I guess my question would be around where those PDFs come from, why they're being updated outside of M-Files, things like that.  Are you able to elaborate a little on the wider process at play here, rather than the specific act of updating the PDFs?

I have a similar issue. We have word files with M-files properties to match different packages. Once we update a word document I need to drag&drop the updated file over existing file for each package.

Is there a better way to do this?

Like Craig suggested it's best to raise this with your reseller as there are many variables and the recommended solution depends on the details of your processes.

Like Craig suggested it's best to raise this with your reseller as there are many variables and the recommended solution depends on the details of your processes.