Would anyone have insight into how I should evaluate these two Pagefile % Usage values to determine the actual pagefile usage on the server?
There are a few things that can be happening here, I'll list them in order of likelihood:
You don't have a pagefile at C:\pagefile.sys. It's incredibly rare for there to be absolutely zero usage. You can check the location of your pagefile(s) by running wmic pagefile /format
from an elevated command prompt.
You have more than one pagefile and the one on c:\ just isn't getting any use. Still pretty uncommon but possible. Run the command above to verify.
You're reading the Perfmon graph incorrectly. Pretty unlikely, since it's straight forward, but worth mentioning since you didn't post a screenshot of it.
Does the fact that the Server is a Virtual Machine have anything to do with why there are two values?
No.