Click and drag to link file to cell?

I need to link to pdf-files from specific cells in a table. Hence, I right click the cell, select ‘Link’ and browse for the file within the file tree and select it. But having to do this individually for every single table row is time-consuming.

Is there any way I could just click and drag the file into the table?

Alternatively, it would be much easier if the files in the ‘Insert Hyperlink’ dialog box were sorted with the most recent file on top, but they’re always sorted alphabetically, it sems. Is there any way to change this?
Down the road I’ll have several hundred pdf files to link to in the same folder and often with relatively similar names, so making sure I link to the correct file becomes even more of an issue.