Are the machines on an IP network?
If so, this may be an option for you.
Download the utility FileSync, it can be downloaded from here:
http://www.download.com/3000-2248-7708520.html
Share the folders, C:\windows\fonts on one of the machines (Machine 1).
On machine 2 ,map the C:\windows\fonts file on your remote computer to a drive letter say Z.
Install FileSync on one of the machines (machine 2) and run it up.
Click Select Folders and set Folder A to the fonts folder on your machine running Filesync (c:\windows\fonts) and the set Folder B to the letter you mapped above, Z (Shared fonts folder on machine 1)
Click Add, then click Save List so the folder references are saved.
Click on Pre Scan and this identifies the files that need to be synced. Then take the option to Sync the files.
Once the process is complete, then the fonts on both machines will be the same.
I actually use this application as part of my backup routine, I back up all files each Friday and then use FileSync every day to update the backup, takes about 5 mins each day.
I hope this is of help.