Docker Architecture Question

I am new to Docker and have a quick question on how to architect my production farm using docker swarm. My current setup includes 30 VM’s running windows server 2016. Each one of them have Java app server with 6 JVM instances hosting 5 different sites in IIS.

Can i run multiple IIS sites with in a swarm cluster ? will i encounter any issues by running multiple JVM instances with in a container and how do i manage swarm cluster on top of JVM cluster ?

Thanks in advance.