Come back Apache, all is forgiven.
So in the small (ok, mega-tiny) chance you visited this site earlier in the week you would have noticed it was slightly more populated then this. This is because I’ve had to re-install the darn thing from scratch again due to more issues with WordPress on IIS. Don’t get me wrong, Microsoft Web Platform installer does make the installation pretty straight forward but I hadn’t accounted for the weird any wonderful issues you only seem to get using IIS. For example, in order to get rid of having index.php attached to all your URL’s, you have to enforce URL rewrites. This took a few seconds using Apache’s htaccess but on ISS you have to mess around making sure URL rewrites are enabled and then create your own web.config file. Next, media uploads flat out refused to work until I investigated why the default NTFS permissions wouldn’t allow the WP App Pool to save to the location.
I guess the advice here is that WordPress can play nice with Microsoft IIS, but if you have a choice – Apache and Linux is so much less time consuming!