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For #1 you wanna try Magic wormhole. Maybe it's less user-friendly than you need it to be, but it works and there are lots of implementations for different owes (don't know about iOS though).
There's also localsend, which works like a charm.
python -m http.server 8000
i would absolutely recommend localsend. it has ios, android and desktop apps and it works flawlessly:
Edit: iirc you need to be in the same network though, it does not have gateway (?) servers like wormhole
That is kind of the problem though. There are many solutions, all with their own pros and cons. But after all these years no universal standard has managed to appear.
You asked for it
I thought it would be https://xkcd.com/949/.
Honestly transferring files over the internet is a solved problem.
Have you tried NordVPN meshnet?
I used to use Pushbullet. Haven't really needed it in a long time since discord came on the scene really. But it did the job really well and was super easy to use.
Cool stuff. How does this stack up vs syncthing? I have a weekly clip show I'd love to be able to share with friends and family
they both do private file sharing, but their working principle is inherently different: wormhole, localsend, pairdrop etc. send a file once, whereas syncthing aims to sync a folder on 2 or more devices bidirectionally
That sounds better for my use case, right? I could send my show out, and not have to worry about whether they deleted it.