How do I setup file uploads to BuddyPress profiles?

I want my members (multisite + BuddyPress + bbPress) to be able to upload files to their profile.

The files will be either pdfs or images. Ideally they will able to upload an unlimited number.

I also want to be able to test to see if a member has uploaded at least 1 file and email the member and admin if they haven’t with a customised message to remind them to do it.

I’ve found a number of possible options, but what approach would you recommend? Especially to allow for the test and email if they haven’t uploaded a file yet.

Galleries customised to accept pdfs too: