I used awk to migrate users from one system to another. I created template scripts for setting up the user in the new system, I dumped the data from the old system, then used awk to process the dump and create scripts for each user in the new system. That was a fun project.
Docker is a moderately sized step beyond VM.
I might recommend setting up VMs with something easy like VirtuaBox. When you have that figured out move on to Docker.
If your a casual user VMs are likely sufficient.