Tuta Drive is being worked on, and we are constantly improving the interface (the calendar has seen a lot of nice updates recently). About PGP: We’d like to support Autocrypt, but right now we are busy improving TutaCypt (our quantum-safe encryption protocol).
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Challenge accepted, we love Linux 
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We do have a family option: Introducing the Tutanota Family Option! | Tuta
Please note that each user will cost €36/year and each gets 20 GB of storage, so most likely Revolutionary is the better option in your case.
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Aliases are supported, but we need to work on making the management of aliases more convenient. It’s important to note, that with your own domain, you can use an unlimited number of aliases!
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Is it possible to add Holidays and a year overview to the calendar?
With any paid plan, you can sync external calendars like holidays. A year overview is not yet available, but I’ll pass this on to the developers, thanks for the suggestion!
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