In Win2008 VM’s Settings, define under COM1 create a named pipe with a name like MyWin2008VM.
In the VM itself, in an elevated window, do: bcdedit /set debug on .
Assuming that the Hyper-V system running the VM is itself named MyWin2008HV, start windbg on the Win7 system (or on some system; couldn be the Hyper-V system itself): windbg.exe /k com:port=\MyWin2008HV\pipe\MyWin2008VM,pipe,resets=0,reconnect .
Reboot the VM. The debugger session should show activity (assuming there are not network/firewall issues.)