The question I have to ask myself repeatedly about consumer technology is “what does the manufacturer expect ‘normal people’ to do?” Anytime I’m confronted with moving a video from my computer to a relative’s iPhone or trying to load music from a cloud service into Apple Music/iTunes, I ask myself this and usually just conclude that normal users would give up and I do too. Then I crawl back over to my desktop (running OpenBSD) and pretend to cry.
My sister-in-law asked me to rip a cd so she could play some lullabies for her son. I did. Then she asked me how to copy them to her iphone. I could not figure out a way to do it. So I turned the thing into a static html page with <audio> tags so she could play it. This seems comically user unfriendly, or maybe even hostile from a company that's supposed to "just work".
I honestly don't remember whether I tried iTunes, but it sucks either way. Either I tried and couldn't figure it out. Or maybe that's the only way to do it and I didn't try it? Which means you need some heavy proprietary software to copy a file. Every non-Apple mp3 player or smart phone that I've ever seen lets you use standard protocols to just move media around without setting up user accounts or synchronization settings or god knows what.
Just fyi: easy up-/download options via USB have been degenerated on Linux as well. MTP (which Google pushed to replace mass storage device mode) is hit-and-miss on Ubuntu; for example, it doesn't work with S8 and newer at all. MicroSD doesn't work with newer/larger cards, Bluetooth is a clusterfuck ... in many ways, the last decade has been a desaster for interfaces people care about.
I remember ~10 years ago i used Automator with Folder actions (or something called like that) to setup automatic resize and transfer of videos from a folder to my iPod Touch through iTunes, so my guess is that iTunes would do the trick. Unless they broke it since then.
For future reference, you can download VLC from app store, it has a local wifi server which you can connect to from pc and upload media files from browser.
