For everyone who has not already, this is so worth a read: https://www.gnu.org/fun/jokes/ed-msg.html
Radicale? https://radicale.org/v3.html I have not used it much myself yet. Its very minimal and focused on calendar stuff.
The key needs to be available to continue to be able to decrypt the data on the device. All encrypted data is not decrypted as you mount or unlock your encrypted device, that is done one the fly as you use it.
The attack you are thinking of should also not be relevant. What you worry about appears to imply that you are more concerned about the key being protected, rather than the data the key protects. You seem to wish to have your decrypted data available, but not the key.
Oh, it is part of the Tor project even. Cool. Thanks. I will read the links.