Although FileVault gives more security and remote access presents a relatively seamless experience when you sit at your computer, the reboot authentication requirement for FileVault does pose a bit of a problem for you, whether you apply Screen Sharing, SSH, or any other remote-access technologies.
You here can run a certain command line in the destination device to restart a FileVault-protected system and return it to a working state:
sudo fdesetup authrestart
This command will ask for the current user's password or the recovery key for the FileVault volume, and then store the current user's credentials so when the system is restarted the computer can use these credentials to unlock the reboot screen.