ArcterJournal explains how the various wizard controls for things like IIS aren't as helpful as you might think - sometimes, all you need is a small hammer:

The thing that probably pissed me off more than anything was the complete lack of some simple tools to help me make it work. The lack of a decent command line, or decent tools to help with debugging in windows pisses me off horribly. All I wanted was to "tail -f logfile" in a terminal the width of my screen so I could see the debug information flowing through. Nope. The file was big (and undeletable because IIS had it open of course, thanks for that great filesystem Microsoft, maybe WinFS will fix this?) so doing a 'type logfile' was a huge pain (especially through a VNC connection), notepad didn't deal with some of the CR/LFs properly, and wordpad isn't in the default command line path, all culminating in me getting really pissed off that such a simple task as watching the contents of a logfile should be so hard. Cygwin or other additional apps? Remember, live client machine, not the place to start randomly installing software. Oh, and don't get me started on the so called "Event viewer" or the stupidities of IIS itself.

I have no idea how I'd manage this server remotely with Windows tools. As it is, all I need is ssh and a shell...