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The fucking bane of my existence I swear, all my homies hate filesize limits.
Fortunately we have a few options, some better than others, and if it helps one person Imma talk about it now.
Magic-wormhole: My favorite, CLI client that shares files from your computer to a server to be downloaded with a password you send through your normal means of communication. No filesize limit, files stay on the server for 1h unless downloaded (deleted after download.) For sensitive information I would PGP it before I upload but I have trust issues.
Warp: Magic wormhole, but GUI. Second favorite, only because I love my terminal so much. It's literally just a GUI wrapper for magic wormhole though so no complaints from me. Works on windows too iirc, and the android wrapper for it is called just "wormhole" alone, no "magic."
Onionshare: Sends files directly from your pc to theirs, works through Tor. I have gotten it to work before, but sometimes it hates me and refuses to connect, usually when I try to DL from mobile.
Soulseek: Not exactly private, but it works if you can forward a port. If you need privacy you'll have to mark the files as private, probably name them something nondescript like "file1," and set it so only your trusted buddies can download it, then whitelist the buddy you want to share it with for that time (would have to remove trust for buddies by default, only enabling the ones for the current file to be shared, then swap that again next time. Like I said it "works" but it's far from ideal. Would also PGP them files to be safe.)
Torrents: well we all know this one, it's the classic!
I'm probably forgetting some/don't know some, so anyone else feel free to add!
The classic would probably be plain old FTP, but SFTP/SCP/SSH works fine as well.
When I need to share files to newbs I usually just use a small Node script to host an HTTPS server from terminal, and give them a file link
I remember being shown FTP back in high school and finding any reason at all to use it, in spite of the fact there were better alternatives for my friends to access certain files, especially considering I probably got the shit of Kazaa anyway. But we FTP'd, and it was slow most of the time, or slower than any of the shares, but it felt good.