It depends on how you are doing your vpn.
If your vpn server has the capability to accept a connection which specifies an IP address to use, and your client supports requesting a specific IP, you win.
We use this technique for remote users on Win95 to print complex documents to their local printers from a central server. It also works with Shiva dial-in servers and the like.
To make it work, assign each remote vpn user a fixed IP address. This may be a "real" address on your network, or may be a 192.168.x.x address, in which case you will need to route these addresses in your internal network.
Scenario: User John Doe is assigned 192.168.1.101 and that number is put in his client software. John connects to the internet (with adynamic address), and starts his vpn client. The client contacts the server, requesting IP 192.168.1.101, and the server authenticates him and lets him use that address. John now has a known address on your network, which can be put in your printertable.
Good luck.