WordPress: Can I batch upload lots of files (e.g. via a custom field) which will appear on my website as a list of downloadable files?

TL;DR: Can I upload hundreds of files via WordPress (vanilla or with free/premium plugins) which will appear on my website as downloadable files, or would another CMS be better suited to this task?

More info: I'm building a site to replace an old WordPress MU site. My (non-technical) client needs to be able to create a single profile page for each of their employees. Each employee page must include some or all of:

• A header image
• A text intro
• A photo gallery
• A list of links
• Multiple audio embeds
• Multiple video embeds
• A list of ~1000 downloadable files, mostly pdf/jpg, divided into subgroups

Ideally the last point would be achieved something like this:

1. Client adds a custom field and must name it
2. Client drags any number (realistically 1-100) of files onto the field, or uploads via "add files" function
3. Files are saved in the backend to a folder named after the custom field
4. File order is editable by client
5. The field is output to the HTML page like this:

<h1>Custom Field Name</h1>
<ul>
  <li><a>file1.pdf</a></li>
  <li><a>file2.jpg</a></li>
  ...~100
</ul>

Employee A is totally separate from Employee B, C, etc. All employees' pages will be managed by a single user. Their files should exist separately in the backend. The paths to their files will ideally include their name, but only the filename itself needs to be printed to the page. A file system like this would be perfect:

/EmployeeFirstName-EmployeeLastName/Media/YYYY/Filename.xxx

I believe WP's default media file save directories can be customised via plugins.

I'm trying to do this in WP because it's what I've used in the past and it's what my client is familiar with. A friend recommended the Advanced Custom Fields plugin for WP, which I am looking into. I'm an experienced designer but a beginner developer. I accept my naïveté and I'm keen to learn.

Possible structures:

• A single WP install with a Page per employee
• A Multisite WP install with a Site per employee
• Other?

After much searching I'm beginning to think WP might not be a suitable platform for long and busy pages (~80 video embeds per page, added via ACF) with this type of file management requirement. The admin page for my test page is already very slow to update and I haven't even started the file list part.

Since the key feature of this page template will be the ability to list hundreds of downloadable files, it seems logical to me to pick a CMS based on that requirement, rather than pick a familiar CMS and try to force it to do what I want.

Thanks for reading!