PDF Assets - Uploading pain points



Hey Assets Community!  I've been tasked with exploring ways to improve our current AEM 6.4 implementation with workflows and one challenge is pretty simple: uploading/replacing PDFs in our DAM. 

We have several documents folders that contain 70 or so PDFs that get updated quarterly.  Right now this is a manual process where we rename the PDFs locally to match the target file on the DAM so it is replaced.  We don't use versioning. 

Where would we begin to develop a more elegant way of uploading PDF assets into a folder without having to match up the filename manually?  I have a general understanding of the Assets API, and have read some discussion on this topic.  Are there any OOTB solutions that I've missed?  Will this require a ton of custom development?

Thanks for your advice.