I hate windows server. It can fuck off for life. So glad I have nothing to do with it. Now off to use my Debian experience on RHEL and SLES
I have a love/hate relationship with windows server.
Generally everything is point and click and turn key and makes things easy to manage.
On the other hand Windows has some of the worst annoyances, and it also does not help that most commercial software is very badly written and you are almost guarantee to run into issues, which, because it's not open source, is not easy to find a solution for.
Don't get me started with the arcaic licensing schemes of commercial software. All these artificial limitations just to make you pay even more money than you already paid.
On the other hand, some stuff in Linux can be frustrating too, like dealing with it's primitive permission system and the fact that you have to sync uids/guids across all machines etc... and the fact that it does not have inheritance so if a different user writes a file it does not inherit from the directory... this makes for a very messy file system where all the permissions are all over the place if it's a multi user network. I can't imagine managing a corporate file server with that crappy permission system, especially considering some of the crazy permission requests some people ask for at times.
Though the fact that it's open source means all this could be improved with some customizations. Eventually I want to write a distro (well more like take a distro and modify it) and make it more turn key for server stuff and completely rewrite the permission system so it's more like NTFS.
If I had to pick I'd want a full Linux environment over windows, though, but Linux would require lot of customization to be as turn key as Windows in some respects, especially file permissions.
Disclaimer: I have not used windows server since Server 2003 and touched 2008 slightly. I hear the latest versions have metro. Fuck that shit!