Hello, sorry to hear about your trouble and I am glad you explained it better in this post than you did to me in email a few minutes ago.
It doesn't sound like you're having issues with the web site, or the license server -- which are both running fine.
Rather, it sounds like there is an issue with the software on your PC. If you were having license server issues you wouldn't have to kill processes with task manager, you would get a message indicating that it couldn't connect or failed to access your account, etc. Normally the first thing anyone does when having trouble with the license server is tell me what message they are getting, or the error number, and ask how to fix the error number.
Edit: the only way I can get 2 instances of Rift to load is to load the default Rift profile and then my character set.
This is particularly telling that this is probably not related to the license server.
Open the main Inner Space console to see what ISBoxer says it is doing when you launch your Character Set. Instructions here:
http://isboxer.com/wiki/Console. If you don't understand it or it doesn't help, paste me the last 5-10 lines or so from the console when you launch it, and try to explain in detail what you do and what happens, when you try to launch your team.