How to shrink a DigitalOcean droplet onto a smaller disk option:
Spin up a new droplet
install rsync and...
rsync -aAXvP --exclude={/boot/,/dev/,/etc/fstab,/etc/modprobe*,/etc/modules/,/lost+found/,/etc/mtab,/etc/network*,/etc/sysconfig/ip*,/etc/sysconfig/kernel,/etc/sysconfig/network*,/lib/modules/,/media/,/mnt/,/proc/,/run/,/sys/,/tmp/,/var/lib/lxcfs/,/var/lock/} root@LIVESERVER:/ /
Reboot the server and away you go. Not battle-tested - please take snapshots/backups as you go!