Assign differents files to differents users

Hi,
I need assign for example 500 differents files to 500 differents users, like so:

user_name_1 -> File “1.pdf”
user_name_2 -> File “2.pdf”
user_name_3 -> File “3.pdf”
…
user_name_500 -> File “500.pdf”
With your plugin I can do that, but one by one, so it is very hard (a lot of time…)
I’d like to have a new feature, where administrator can upload a csv file with the following columns:
User Name – File Name
So administrator can build the following csv

User Name – File Name
user_name_1 – 1.pdf
user_name_2 – 2.pdf
user_name_3 – 3.pdf
…
user_name_500 – 500.pdf
The process is the following:
STEP 1: upload the .pdf files
STEP 2: upload csv file
When the csv is uploaded, files will be assigned to the correspondent user, and it no is need to assign file one by one.

I hope you are understand me.
Can you make this new feature?
I hope your answer. Thanks for your support.

https://www.ads-software.com/plugins/sp-client-document-manager/