So tonight, I decided to pay this some attention and attempt the update. From the begging I ran a HDMI cable from the back into my middle console, just in case. So I have the Lightning to HDMI AV cable + USB Lightning cable ready to go. So I open the USB port up on the old 30 PIN and plug in what will soon become a parade of USB thumb drives.
The update that came out last July wouldnt update either and Pioneer sent me the update. Because it went on back order, my local Best Buy helped speed up the process and was able to update it with the USB thumb drive they found that works on their demo units. So I saved the Pioneer thumb drive for such an occasion as this one. I tried downloading, extracting the files, and moving to the thumb drive in both MAC OS and Windows 7. I started with the YUK file both times. I get cant read UP file when I plug it in.
Pioneer wants me to take the unit out, pay them $60, and ship it to them for who knows how long they will have it. Meanwhile, I will have a whole in my vehicle dashboard, no music, radio, etc... at all.
I think I will be calling Best Buy to see if they have had any luck. I didnt plan on visiting them until I got the cable from Pioneer and have them clean up the cable run clutter for me. But maybe I am going to have to see if they can even get theirs updated. If so, their update may work on mine.
The way I see it if their's screws my unit up, I am no worse off than my other option to send it away to Pioneer. At least BB will be there to unhook it all for me. 
I hope everyone else is having better luck!
Chad