If you're using a workstation version of windows (XP or whatever) you are restricted to a single website, so if you're using the box for development you can't duplicate the web structure of your target server. Each of your development websites will probably be virtual directories under your root web and when you transfer to the web server you'll probably run across many broken links and includes.
Easiest would be to use a server OS for development.
I didn't attend the funeral, but I sent a nice letter saying I approved of it. --Mark Twain