Anyone that can update me on the current state of this combo? Docker possible? Virtual machine 
hassio has a built in docker container manager/supervisor. So it would be redundant to run a docker manager inside a docker container. Instead look into setting up the home assistant docker container and then setting up the docker containers for whatever else you want/need. This is what I do. I then have the containers linked as needed using ip:port notation in the component.
Synology DSM with docker containers:
- let’s encrypt
- home assistant
- mqtt
- mariadb
- homebridge
- dockermon
- unifi
- influxdb
- grafana