I've been trying to accomplish the same goal, and have come to the same brick wall. Have you had any developments lately? Some of the tips you give here are great, thanks.
I also pursued making a jump drive bootable, thinking that would get me closer. It worked, but still no autorun capabilities. Here are the two utilities I found to do it (if you don't already have them). This is the one made by
HP (follow link), and the other is a Lexar utility (file attached), but it is my understanding that they will work on any drive.
What is very interesting is that the Lexar utility has a "Flip Removable Bit" button. I know, seems like exactly what we are looking for, but I have not been able to get it to make the drive autorun when inserted. Maybe you will have better results. Let me know what you find out.