Multiple attachments for each Drawing No (Autocad file and a Excel file)

 I would like to make a drawing management for my self.
I have made a list that it has some columns like below

Drawing no
Title

Also I want to make a document library that it has lookup column to the drawing no column of list.
Now I want to attach a Auto cad file and a Excel file for each drawing no.

Now i do not know for solving my problem and also controlling versioning:

• I have to create Document set and put files of each drawing no inside folder. Also I do not know how to control versioning of Document set Automatically Because I read on the Net versioning of Document set is done manually. I would like when I modify a file inside a Document Set, Version of Document set Also change.
  
  Or
• I have to upload each file one by one and then select drawing no from lookup column.

I have this question for more than of 1 year in my head and because of that i have tried to learn SharePoint, I appreciate for any helping in this regard.