Have you checked out pet sets[1]? The last couple of kube releases have introduced some really nice work to help with these cases
Edit: You can find Helm charts here: https://github.com/kubernetes/charts/tree/master/incubator
For instance, would a complete Windows Server instance fit the Pet Set concept in the scheduler?
PetSets are simply ordinally ordered container collections instead of randomly ordered.
The usual concept in Kubernetes is that a container has a name like 'thing-randomsuffix4242'. It is pushing you towards making your pods stateless and not precious so the failure handing logic is simple. If it is blown away for whatever reason can easily be replaced by the scheduler and 'thing-randomsuffix242b' is never far away.
With a predictable ordering you can actually make assumptions you otherwise couldn't. For example, perhaps you want the convention that 'thing-predictable1' is the master and 'thing-rpredictable{2,3}' are the slaves.
so rather than 'kubectl -v', you will run 'hyperkube kubectl -v'