How to shrink a DigitalOcean droplet onto a smaller disk option:
Spin up a new droplet
install rsync and...
rsync -auHxv -exclude etc/udev/ -exclude etc/sysconfig/network-scripts/ -exclude proc/ -exclude tmp/ -exclude sys/ -exclude dev/ -exclude mnt/ -exclude boot/ root@LIVESERVER:/ /
Reboot the server and away you go. Not battle-tested - please take snapshots/backups as you go!