There is a fair amount of evidence in psychology that previous experience can be a significant obstacle to learning new things in certain situations. I believe that new software is a good example of this, especially when moving from “strict” applications that expect you to use certain features in a particular way, to “looser” or more flexible software like Tinderbox, which provides lots of opportunities for doing things in different ways, and fewer constraints. I feel that to some degree it is up to the user of Tinderbox to invent their own way of doing things. Others might disagree, but that is roughly how I see it.
A couple of years ago I inadvertently started off a discussion that you might find interesting, though I suppose it might also be confusing – in any case, it is here if you would like to look at it: http://forum.eastgate.com/t/user-attributes-or-tags/1069?
I think one of the main things I took away from the discussion is that Tinderbox is perhaps better for associations than for hierarchies, and that there are various different ways in which those associations can be made, and displayed, in Tinderbox.
My experience has been that letting go of old paradigms is a good idea when approaching Tinderbox. One of those old paradigms from database software is that you have to set up all the categories and so forth before you enter any data. In Tinderbox it almost seems to be the other way round – you enter the data and let the categories emerge as you work with the material. Tinderbox facilitates the thinking process.