Ok so an update....
I called the DMV and had to re-fax everything that I sent 3 months ago when this crap happened. I also had to call the insurance company to have them fax over proof of insurance from the time period in question up until now.
YAY!!! Got everything done, right? NOPE!
I called the DMV to check up and make sure all the documents made it there. I'm glad I did because apparently the original person gave me the wrong damned fax number. According to this new and very helpful person the process to clear this colossal **** up would take 7-10 business days from the original fax number. Cue lots of swearing, angry tones, and general increased blood pressure. (WOOHOOO!) So the nice lady gives me the fax number directly to their department. She then tells me if everything is sent to that number it will be resolved in 24-48 hrs. I'm impressed at the moment.
Now back to the insurance company... I call them back up and sit on hold for 20 mins. Anger and blood pressure are rising at this time due to one of my students being sent back from a high risk trainer due to sleeping in class. Much yelling ensued and I do believe I scared the crap out of him. Insurance lady answers and tells me that she can't fax over the information because she is not licensed for CT..... Transfers me to another agent and I get to sit on hold for 10-15 more mins. I get the insurance info sent to the right fax number this time.
Now the waiting begins......
Note: It was very hard to keep calm on the phone during these entire proceedings. I did slip though.