[PROBLEM SOLVED]
There was a caching issue with the Windows Firewall or something. I think I undid my firewall steps at some point during the software/firmware updates.
If you're experiencing the same issue, please check out the "read this" thread and double check you followed the steps in the correct order and/or your steps do not get undone in the process:
http://forums.pioneerdj.com/entries/20118251-Read-this-thread-before-posting-for-help-with-rekordbox-
Cheers :)