Bill,
NI will chime in at some point, but so far the crowd here is proceeding exactly as an NI AE would likely do.
I can verify the undesirable behavior you are describing (I ignore all I/O-related errors, as you have suggested), but it's not clear from the thread so far that you've found a LabVIEW bug instead of a coding problem. It's definitely impossible to conclude bug/non-bug just by playing with the EXE, because the nondeterministic behavior you have described could be caused by race conditions arising on your block diagram that create different outcomes in IDE vs. EXE, machine 1 vs. machine 2, etc.
It would be possible to conclude bug/non-bug if we could examine the LabVIEW code. If that's not an option for privacy reasons (and if you can't make a stripped-down version to post), then I imagine the NI AE who joins the thread will have to e-mail you to get a look at the code privately.
Question: the UI seems much more complex that you suggest, unless you have done some really fancy control customizing. It seems as if the combo box is displayed in response to a button press, and that the resulting user choice is written back to a separate string indicator: three elements instead of just one listbox. Is that correct? Because of the apparent complexity, it's easy for an observer to suspect that a coding mistake is causing the problem.
My thoughts,
John