Password protect some uploaded files, so only logged-in users can view them

See my question and answer again, you linked it already in your question:

simple solution for restricting access to (some) uploads/downloads

The solution isn’t that hairy the only necessity – besides configuring the plugin correct – is to create a .htaccess, which you could do programmatically. For that you have to automate the creation of the .htaccess file inside the configured folder of wp-downloadmanager. On the other hand, you obviously read that…

You might want to take a look at this solution:
https://github.com/mattheu/Private-Media

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