droplan
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run continuously
trafficstars
I think it would be nicer to run droplan as a daemon process that continuously ran so that it could better splay out requests to the digitalocean api and more gracefully handle throttling.
Together with this you could also listen on certain port on public interface for http requests (with some shared secret) that when invoked would trigger an update (so that each server would reach out to DO).
Secondly, when starting the daemon, since you already have list of droplets you can make the above request and have everything up-to-date with no cron :)
Removing a droplet would be a special case though.