And I am genuinely curious as to why you think 12 Windows servers are pain compared to 12 Linux boxes?
The last time I had to work on windows servers SSH wasn't really an option though so we used remote desktop. This was on win2k servers though so things may have changed.
I think the question deserves a better reply than the glib "The same way as you administer any cluster." Is the answer really SSH? Or something else?
There are a few ways of dealing with IIS7:
* Remotely using IIS Manager 
* .NET-style configuration files - think httpd.conf
* Powershell cmdlets
SQL Server has Management Studio in various flavors, SqlCmd.exe or Powershell cmdlets.
The only time I log in to servers is to run installers or when laziness takes hold. These various tools work well enough that Microsoft offers Windows Server Core which only provides CLI access (and Powershell in the most recent version).
The idea that Windows can't be scripted hasn't been true since Perl 5's COM module in the 1990s... Haters always hatin'.