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Same here, try to de-google my life while sitting comfortably in the Apple ecosystem as the happy hypocrite that I am. But the ecosystem is also the main reason to stay, not that it is hard to get out, but it is just a vastly superior experience if you don’t want to spend unlimited hours to customize every goddamn setting. Also, the ecosystem’s main feature ‘continuity’ is unmatched on other systems.
No, as a webdeveloper I don’t know anything about your custom windows server environment and how to share files between all kinds of devices on it.