Encryption solution for dual boot shared drive with cloud storage?

I already have a non-boot shared NTFS partition, which I can access fine in Windows and Ubuntu, and I use Insync to backup a directory on it to Google Drive. I would like the data on Google Drive to be encrypted, but seamlessly decrypted whenever I am logged in to either Windows or Ubuntu. I am also interested in encrypting the entire drive, though I appreciate this may be overkill, and a bad idea for some reason. Once configured, I would like to replicate this on my laptop, without encrypting the entire (boot) drive - for now.

Is the following feasible, or can it be done better somehow?

  1. Encrypt drive with VeraCrypt, and to automatically decrypt whenever logged in to either OS
  2. Configure Insync to backup either the entire drive, or a top level directory of it
  3. Configure Cryptomator and point it either at the drive, the Insync directory, or a directory within. This should also automatically decrypt whenever logged in to either OS.