You really need to be able to "mount" the ripped DVD
as a DVD in order to access the menus, etc. There are ways to do this, but Windows Home Server has nothing built in to support it, and you will almost certainly need to do it "locally" (i.e. you won't be able to stream the menu interaction from one computer to another). One answer would be to use Windows Media Center on a home theater PC; it can be configured to include a network location as part of it's media library. You would point that to your home server, and connect it to your television.
You'll probably get better information (and maybe some other solutions) on
The Green Button.
I'm not on the WHS team, I just post a lot. :)