As I alluded to in my previous post, there are a number of different transport protocols to use with winrm, and it was quite good fortune that the docs had caught up as I was playing with them all. The last one on my list was CredSSP, which is probably the best authentication method in my mind!
Managing a Windows environment at a relatively small scale usually means a lot of manually crafted virtual machines. It’s just the nature of the job. The infrastructure doesn’t frequently change, time is stretched and budgets moreso.