Yes it is possible, you just need to adjust the portal's role e.g document (edit : all) to allow him to edit all document in the system otherwise (edit: account) to allow them to mass edit all documents related to his account/accounts.
Also make sure that you have (Mass Update Permission set to not-set or yes) in order to allow the to select multiple records.
As far as i know there is no function that allow to mass download files from the system.
I hope this helps
Multiselection in Portal
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