I’m new to WordPress and in a few months will be attempting to set up three blogs. They most likely will be hosted on a Windows Server with IIS. (because the server is already there, and nobody else would know how to maintain Apache) The blogs will be unrelated and not share any common users.
My question is, are there any benefits in this case to doing a multi-site setup, or would it be much simpler to have three separate WordPress installs? If we’d go with separate installs now, would it be a hassle to combine them into one multi-site install in the future? I’ve read that multi-site on IIS doesn’t work very well.
There’s really great WordPress codex article Before You Create A Network, “Do you really need a network?” part will answer most of your questions.