I really like the idea.
syncthing is a strong recommendation for this. Itll start manually on my host. and then simply sync my files semiautomatically whithout the need of having to run my rpi all the time especially if I still use it to experiment.
My initial reaction was basically one of your headlines - "Desktop apps with extra steps". But I guess you are right that selfhosted apps are often better than plain desktop apps. Interesting idea in general.
A cool thing to have with this would be backups, designed in a way that makes it easy to manually back up on a USB drive. Not necessarily automated, but maybe with automatic reminders "You didn't back up your data in X days - Backup now - Close".
A place to share alternatives to popular online services that can be self-hosted without giving up privacy or locking you into a service you don't control.
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