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The update method should work. If the DO files are missing, you can create a new droplet and replicate them. If you can deal with the downtime, I recommend taking a DigitalOcean snapshot of the 11.3 droplet and creating a droplet based on the snapshot. Apply the update to that, and see if everything checks out.
FYI, I prefer to use iocage to manage FreeBSD jails with a lightweight host system so that all configurations and data can easily be transferred, backed up, and restored using jails.
Good luck!