this post was submitted on 26 Jun 2023
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I read your workflow. My suggestion is don't use a messenger, use syncthing or a similar app on a local shared storage. it's way better. you wouldn't get duplicate files, it does its thing automatically, you can even have versioned files. and it's not THAT hard that your parents won't learn. pretty easy and straightforward.
and for messaging, you can use matrix, IRC, briar.