The 'file' type field & how to use it

Just got the tip about being able to upload files & images, and was intrigued to find out how this enables "No more ... manually storing and uploading files one by one." I clicked the link for more details, which took me to the documentation on customizing fields, the only mention of files being the file-type field. Interesting, but it would be helpful to have some use-cases explained. 

For instance, we have a set of about 60 customers who get a individualized report once a quarter. To do that now requires either manual attaching of reports to individual emails or establishing individual downloadable files on Ontraport with related links--neither very time efficient. Being able to refer the client to a special page where they could collect the latest report file would be efficient IF we could get the quarter's reports uploaded in one fell swoop, like we do some updates now using a CSV import. Is it possible to update a file-type field with a group import? How? 

How else has the file field been used to do away with 'email attachments, expired file links, or manually storing and uploading files one by one'?