Are you using directory services (Rio 9.2)?

Follow the instructions in this link to make sure the legacy ports are open (http://www.laserfiche.com/support/webhelp/DirectoryServer/9.2/en-us/Admin/Default.htm#Ports.htm%3FTocPath%3DConfiguring%2520Licensing%2520Site%2520Settings%7C_____1)

You mention the server license is not being validated - did you manually run showhwfp.exe on the new server? Since they are not in the same domain or workgroup the Rio server can't connect to the LF server to get that information automatically. But you should be able to create a key manually with that HW Fingerprint once you have it. 

At that point you should be able to manually transfer over they key and if the ports not blocked you should be in business. Also, don't forget to assign user licenses to that key before you create it, otherwise you'll have to do it all over again. I'd say in this situation I remember that fact about .1% of the time and almost always have to do it twice myself.