I have been in a similar place lately. We have a primary rails application with 1 other web service and a DB. We looked at docker machine, docker swarm, and t

I have been in a similar place lately. We have a primary rails application with 1 other web service and a DB. We looked at docker machine, docker swarm, and tutum (now a docker hub feature). None were very clear to use. Right now we've settled on Kubernetes and couldn't be happier. It was quite daunting at first as their docs aren't very newcomer friendly, but after a few youtube videos to get the ideas straight, it feels like the perfect way to deploy and orchestrate dockerized applications. You mention using Digital Ocean - you should reach out to Bryan Liles there, who is a super sharp and friendly guy and can help you with Kubernetes on DI. We'll probably be using Google's stuff for our deployments, but with Kubernetes it really doesn't matter anymore. Hope that helps!