Upload directory contents

Let me preface this post: I don't know anything about this at all. Because I don't know anything, I am hoping my ignorance may somehow luck into outside of the box thinking. 

My customer's file storage is huge. 

We've determined that the Upload directory has 139 GBs in it. 

It's not really my job to fix it but I am frustrated and want to help. 

Obviously, through my research I've figured out what a GUID is. I've read a million posts on club and elsewhere to see if there is a way to figure out from the GUID what the file actually is. I understand we can set a date range and just have support blanket delete up to a certain date.

Is there any way to use the GUIDs in the directory to determine what the file actually is. For example: 

Let's say you have this: 
00019efe-6622-11e6-aa95-02a6691319f3
Can you use that to backtrack to what this actually was?
When Sugar generates the GUID there must be some criteria it uses to create that right? Can it be reversed so you can tell anything about it?
Second question: This might be even crazier than the first. Not sure. 

Could you somehow move the contents of the upload directory out of Sugar to an external place and then point to that external place without screwing up everything? 
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