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Hi Grace,
Thanks for your updates. Based on your description, you would like to add attachments in 2 columns in SharePoint List. It is not feasible to achieve it. There is no attachment column type in SharePoint lists. You can try the following:
1. Use InfoPath. In an InfoPath form you can add an attachment field that allows a user to embed their attachment in the form (doesn't go to a SharePoint column, would need to open the InfoPath form to view the attachment).
2. Use a document library.
Given this situation, we welcome and encourage you to share your ideas through SharePoint User Voice. Your providing feedback is the best way to perfect our products and services.
We appreciate your understanding.
Yoga