2008 Server Windows on Connect Media Windows
Here's how you do it:
1. Find a copy of Windows Media Connect 2.0, this is no longer provided my MS but can still be found around the web. Another place you could potentially find it is in the file umupnp.exe on the Windows Home Server installation media.
2. Now out of the box this won't install on Windows Server 2008, so don't bother trying, you need to extract the files from the archive.
3. Create a folder, for example C:\Program Files\Media Connect
4. Copy the following 3 files which were extracted from the archive mentioned in the last step into your new folder: wmccds.exe, wmccfg.exe, wmcsci.dll
5. Run regsvr32 "C:\Program Files\Media Connect\wmcsci.dll"
6. Run "C:\Program Files\Media Connect\wmccds.exe" -installwithfiles
7. Run sc config "WMConnectCDS" depend= none
8. Run sc config "WMConnectCDS" depend= upnphost/HTTP (These 2 commands are essentially an easy way to remove the HTTPFilter service dependency which does not exist on Server 2008. It's functionality now resides in HTTP, I could of done this from the registry as well but in my experience that requires a reboot)
9. Enable the SSDP Discovery Service by setting it to manual startup from the GUI or using sc config "SSDPSRV" start= demand
10. Enable the UPNP Host Device Service by setting it to manual startup from the GUI or using sc config "upnphost" start= demand
11. Run wmccfg.exe and do the initial setup.
From this point you've got media sharing running that is basically the same as the WMP sharing feature (maybe even a bit more appropriate for a Server environment), and it can be reconfigured using wmccfg as needed.
As a side note this works for both x86 and x64 versions (including Server 2008 R2). It also works in Vista and Windows 7 as well for anyone who wants to avoid Media Player on their desktop and still use Media Connect sharing.