[XorNot]

Pairdrop was posted on HN a little while back and I setup an instance on my home network. Doesn't work everywhere obviously but it does seem to effectively solve this problem within my household.

https://github.com/schlagmichdoch/PairDrop

[esafak]

It dropped files midstream for me. Name checks out, I guess.

[Jolter]

Does it require self-hosting a service?

[fimdomeio]

no, you can use https://pairdrop.net/