Perseverance pays. As someone else commented, Maple has been around for a while and their are different packages that are kept for backward compatability but may be incompatible with more modern versions. Likewise the basic tools that take advantage of the new packages aren't always in place yet. Now that I have a better handle on this aspect of Maple's structure I am having many fewer issues. I now know how to recognize the symptoms of such collisions.
More specifically, while I was originally frustrated with VectorCalculus I am now quite a fan once I got a hold of how it works. I just needed to translate how I do things on a blackboard (or on paper) to how Maple wants to see it. Beyond that, I also have to be able to explain what I am doing to others.
For anyone moving along the same path I suggest going back to basics. I pulled an old vector calc. book off the shelf and re-examined how to think about the basic definitions (I teach physics, not math, so I tend to take a lazy "let's just get it done" approach to complex math problems). I then saw immediately what the programmers were trying to do and how they were doing it. I also found it helpful to build some visualization tools which will help this coming year as I build some presentations. By going through the process myself and reviewing how I would go about generalizing some of the problems encountered in vector calc I was able to understand the approach Maple was taking.