What router software are you using? Are you trying to set the file up for routing yourself or are you just preparing a file to be sent to someone else to rout? First of all the letters would be routed with the back side up, then simply set the proper depth for the drill points followed by a full depth cut path for the letters.
Then just run the drill program into a cardboad templete
Then just run the drill program into a cardboad templete