Thanks for the details Jeppe. One more question on 2k12: if MSFT gets the quota bug fixed soon, will you be able get back on the wagon using Win2k12?
Actually, the current setup using SSH seems to work even if it takes some extra work. We now have a Win2k12 EC2 AMI that includes FreeSSHD and haven't had any issues (sans the tickets I mentioned ;-)
Winrm does seem like a more natural fit in windows however and would allow us to use clean Amazon AMIs. But to be frank, it also seems like an area that doesn't get so much attention on the chef side ;-(