File transfer sure is hard. Why is it so hard?
If it's iOS to iOS and just 1-to-1 or 1-to-many, Airdrop works well. Many-to-many quickly becomes unmanageable.
For cross-platform iOS ↔ Android transfers, I usually reach for snapdrop. However, for transfers of more than 1gb or so, it starts to get sketchy with phone lock timeouts and background task kills frequently resulting in failed transfers.
I'm not aware of any reliable and broadly available tool that exists in this space. A magic wormhole client for mobile would be amazing. Do you know of one?
I made this page with its name before seeing this appropriate XKCD: https://xkcd.com/949/
At least I'm not alone.