Hey Geektitude!
If you go to the Technical Support Link from the main product page (http://www.symantec.com/business/support/index?page=landing&key=60247) you will find the answers to your issues.
We have some signed scripts there that will allow you to do the windows activation.
Are you using a Proxy Server? If so, this is a known microsoft issue. No product activation through authenticated proxy servers. If not, there are some other things going on.
You want to use these (and possibly other) articles:
KNOWN ISSUES: http://www.symantec.com/business/support/index?page=content&key=60247&channel=TECHNICAL_SOLUTION&basecat=KNOWN_ISSUE&sort=recent
Troubleshooting Windows Activation Settings
http://www.symantec.com/business/support/index?page=content&id=TECH173963&key=60247&basecat=KNOWN_ISSUE&actp=LIST
Go to the TECH176835 link and download the powershells that will allow you to activate.
Make sure to use the same key you use for the Enterprise and Standard Activations. The other key you have should be for the Data Center only activation.
If you need help with this call Symantec Support. (But the above information is the same thing they would use on your system).
Regards