We were discussing the biggest challenges in Tech Comm at the last STC Toronto brunch and we all seemed to agree that the difficulty getting feedback on the effectiveness of the content we create is the biggest challenge. The things that really matter in technical communication is whether users can achieve their goals after finding and reading the docs, and whether that makes a difference in whether they buy from you again or speak well of you to their friends and colleagues. These things are incredibly difficult to measure. You are just not there to see them happen, and it is very difficult to separate their effects from the effects of the work that designers, developers, sales people, trainers, field engineers, and support staff do.
The transition from DTP to structured writing continues to be a bumpy one, and content management issues continue to plague many implementations. In many cases, the content management strategy depends on writers structuring things properly and they fall apart when writers fail to do so. For instance, reuse of chunks of information ought to make translation easier and less expensive, by reducing the amount of text to be translated. But often, chunking presents a problem for translators, as described here, because the chunks turn out not to be as context-independent as they were supposed to be.