i've tried, homeserver hates VMs, though it IS possible with vmware.
My solutions are these:
Homeserver does media streaming - Install ORB on server 2008 r2.
Homeserver does file serving with drive extender - Just when you add a second drive to server2008, and in Disk Manager right click your existing 'file serving drive' and click EXTEND VOLUME (grey unless you have an empty drive available), wham bam infinitely dynamically spanned drives all keeping your same drive letter and folder shares without worry of any "disk full" error messages. Homeserver has that step automated, but we're better than that! Automation is a crutch!
Homeserver has plugins - they suck, and you're smarter than plugins, so...
----------If you want to have a utorrent service on your computer look HERE.
----------If you want to automate backups to your server, use Comodo, NASBackup or synctoy!
----------You can make a domain for all your home computers, or make the shares PUBLIC: (http://www.techotopia.com/index.php/Configuring_Windows_Server_2008_File_Sharing)
----------You GAIN the ability to have a 100% flexible server to do whatever you want, EMAIL, DNS, PROXY, ISA, VOIP, APPSERVING, GAME HOSTING, STREAMING AAC/MP3 RADIO TO ANY DEVICE ANYWHERE!