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You can supplement Chicago95 with an experimental GTK4 theme from the b00merang project https://github.com/B00merang-Project/Windows-95 You will have to install it manually by overwriting your user-level GTK4 config, but then it will give you proper styling with the latest apps, including full support for mobile UX 'convergence'.
(Since it seems that the b00merang repo has gone mostly unmaintained, it would be nice if it got imported to Chicago95 itself.)
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CodeRabbit
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It's probably overkill for what you are trying to do. But I have been using home-manager [0] as a way to quickly restore my working environment.
[0] https://nix-community.github.io/home-manager/
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bismuth
Discontinued KDE Plasma add-on, that tiles your windows automatically and lets you manage them via keyboard, similarly to i3, Sway or dwm.
What level are you interested in scripting? In KDE Plasma you can interact with the desktop UI via JS: https://develop.kde.org/docs/plasma/scripting/
And then for something more sophisticated there are extensions like https://github.com/Bismuth-Forge/bismuth.
It does all feel a little disorganized/wild-west-y compared to say, a .vimrc with a list of plugins and bindings, which is something that makes a system like Nix (or a fully containerized DE of some kind) appealing
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Unusable until moving your mouse to the edges of the screen and clicking makes it hit the scrollbar, or the exit button. Right now it initiates a resize.
Illustrated example from a different compositor https://github.com/WayfireWM/wayfire/issues/570
It's the only DE I'm excited about it so I hope they fix that. Very very promising and the best part is that it made the GNOME people mad.
GNOME: "Sorry I don't see the use case for that, PR closed. Make your own project. "