1. You will need to monitor the Virtual Machine in Orion to see the Sysuptime to Alert when it reboots.
2. You can do this with a Parent Child Map. Basically you will need to put all of the VM Guests into a new Map and save the Map as "VM Guests". Then take that map and put it on your Main Map. By default, if 1 Node in the "VM Guests" Map goes down, the Map icon will turn Yellow.