Sorted out - kind of
I managed to get it working. It is a bit confusing and still don't understand how it works. I am able to add the hidden field and create a new file field that has a different id. The confusion arises from the fact that that id doesn't bind or have a real column association in the data. I can tell you that part of the confusion comes from migrating from Adobe Developer Tools/InterAkt. I see other users who are in the same boat, and some of the concepts are different. That said, I don't see why, for instance, you can't specifiy a field as a file field in the Data Assist wizard. And the hidden/file field combo required to keep the updates from going awry could be built-in to the functionality without the numerous work arounds. Sure you guys are tired of being compared to Developer Tools, but honestly, I could fly through production with that framework. Webassist requires too many modules, wizards, work arounds, fixes, version updates, etc. to be really efficient.
For what it's worth. Thanks for your help.