Anyway, we are using it similarly. However we aren't necessarily targeting different Os's but rather different environments at the build level (ex. different versions of sencha CMD to build our frontend) as well as the deployment application server (ex. different version of tomcat or weblogic for our Java backend)
It really is hard to say what's the best or what's the worst but either way I think you are spot on in the problem you see with software longetivity. There was a recent post here (sorry can't find the link at the moment) about devops addressing that very issue and the proposed solution was to automate everything and think of the infrastructure as code itself that can be versioned just the same as your actual application code.
The techops at my job guys use Ansible to do specifically that. I think you can do it docker but it's not specifically for that.
Read this: http://devopscube.com/devops-tools-for-infrastructure-automa...
I've heard good things about chef and would like to learn more when I have a chance.
More experienced guys: please refute any bullshit you see in my comment. I truly would like to learn how to be better at devops. A lot is objective but a lot is so psychological in how people work together which is fascinating.