Ok look man, we are trying to help you, but sometimes tough love is better than no love at all.
This is what it basically boils down to.
The Ford system is not perfect. It doesn't give you the freedom that it probably should. And that sucks.
Was Ford lazy? Or did they cave into pressure from RIAA? Who knows for sure, but the end result is you, the consumer, have less choice.
The SYNC system is nearly the same in every Ford vehicle with the system (save for the fancy-pants MyTouch system), and all of them have the same limitations. My mustang's SYNC system is pretty much identical to your SHO's.
This means that exploits found in the Mustang's SYNC system will most likely apply to your SHO as well.
Since you've put up with our harassment so well (and, honestly, every new guys gets harassed - just ask Zach44120 or whatever the numbers are about his experiences here), I decided to go and find those threads I was referring to earlier.
Here's a pretty good write-up from a guy who feels about the same way you do about SYNC:
http://www.allfordmustangs.com/forums/2011-mustang-talk/304470-phantom-usb-2-port-sync.html
Read this one carefully. It has links to other threads with great knowledge, and you get to see that I'm a smartass to everybody on the internet, not just you.
http://www.allfordmustangs.com/forums/2011-mustang-talk/294375-limits-usb-thumb-drive-size.html
Also, FWIW, I got this USB drive for my center console. It fits all of my music just fine and is incredibly unobtrusive. It's the LaCie MosKeyTo.