Around 2008 I saw two girls, not too versed in technology, share a mp3 song over bluetooth. At the time I thought that if technology finally arrived at the point where "normal people" could be able to do things that required lots of technical knowledge just a few years ago then we were very close to a future where technology could be a giant enabler of powers to everyone.
I am really ashamed by how wrong I was and how WE allowed things to became so artificially limited.
In high school (2003-2007) it was super easy for any of my friends and I (varying technical levels) to send arbitrarily large files to each other with AOL Instant Messenger's Direct Connect. Honestly not even sure how a non-technical person would do that nowadays.
The closest I've seen is 'send file over message service or e-mail', but this has a decently low maximum file size.
The alternative for larger files is Dropbox or Google Drive or similar and share a link, but there are limits to how full you can have those be, so sending a 5 GB file might be inconvenient if you don't pay for the upgraded service.
For anything larger than that again, I don't think I would do anything than pass a physical flash drive, since there's nothing else that has a lower barrier of entry and I can rely on a random person to be able to use and understand.
I have upgraded dropbox and google accounts and also a VPS, so it wouldn't be hard for me. But for people who aren't big fucking nerds, nothing exists that's as easy as that. Email's limit is crazy low.
I am really ashamed by how wrong I was and how WE allowed things to became so artificially limited.