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I think I am looking for pretty much something like this but for non-tech-savvy users as well and for Windows. For use between family members who live apart.
There's a gui client for magic wormhole: https://github.com/Jacalz/wormhole-gui
Thank you. Late comment, so you may not see it; but this is exactly what I'm looking for and it worked perfectly when I tested it out.

I feel like the market has room for a simple desktop IM + file transfer client based on Magic Wormhole. Something like this, with a contact list, and a bit more polished.

Glad it worked for you, shout out to Jacalz for building the gui client.

Wormhole is designed to work for when you don't already have an established secure communication channel. Once you have a contact list (and implicitly public key for your contacts) PAKEs are no longer useful.

What you have described is basically Signal Desktop.

Oh I think the technical argument makes sense, it's just that as a user, Signal is pretty different -- it's mobile first, using the desktop version requires having the mobile app (and account tied to mobile). It's a lot different than say ICQ in the 90s where the account is with the desktop client.

Additionally, I haven't tried it so I don't know how well file transfers on Signal work, but I assume it's not truly a first class citizen feature on it and if you start trying to send e.g. multi-GB files, I assume it starts to break down like most mobile IM where the intention is to only transfer small files (PDFs etc.) here and there.