As I'm getting more and more familiar with NodeJS and Docker, I'd like to Dockerize the few Webapps that run on this server so I can avoid to maintain different stacks.

I use Digital Ocean virtual hosting and I'm pretty happy with it.

Docker is straigtforward enough when it comes to run some containers for testing or development purposes but when you need to deal with High Availability or auto-scaling, it could become a real pain in the ass to configure a CoreOS cluster with all the layers that comes with it.
You'd need to setup fleet, a reverse proxy