I see several threads with booting issues. Mostly I think UBoot is the issue, but I don't have any real evidence.
But I think this issue, whatever the cause, leads to other problems. People try to fix the boot problem and end up making things worse. I see a few support threads where that is clearly the case.
I don't know what causes the booting problems, but I can say much of the discussion here revolves around that issue. In my case, the solution was to find USB drives where the problem didn't occur. As I mentioned in the uboot forum, I am not convinced it's really a hardware problem, but at least I have dockstars that do reliably boot into debian every time.
In my case, I have 5 USB flash drives I have messed with. 2 of which work correctly. It's not a real big sample size, but still it's 40% success... not real good. In one thread people are mentioning drives that worked for them. I'm reluctant to do the same because I have 2 drives that should be identical, but only one boots to Debian in all circumstances.
Anyway, my solution of finding working hardware isn't all that satisfying. It would be nice to fix this problem in software if possible. It would be nice to get everyone booting 100% reliably using any flash drive for one. In my case, the main motivation other than "solving the problem" is because one of my working drives is 8GB when I only need 1GB. In other words, to switch drives so I don't waste space.