During our assessment, we identified that there was a lot of task-oriented help documentation written, but that it almost seemed as though it could use a little higher (or theoretical/contextual) explanation of some of the tasks listed in the doc. Basically, a description of the task's purpose and context above the task steps and below the title of the task. Further, upon installing the register software on the iPad, we also identified that there was definitely need for a "Getting Started" tutorial that would be served up the first time logging in.
Today, I was reading the results of an assessment test in Handbook of Usability Testing by Jeff Rubin and Dana Chisnell. The situation and prognosis was the same as our above mentioned findings.
"When users were prompted to try the help, it was found that the organization of the help topics needs to be extensively revamped and made more task-oriented. Even more theoretical, contextual information needs to be included for the most advanced users...It is possible that an interactive primer for users may be required for infrequent but important tasks."Yes, this is likely a coincidence. Here's the point. It seems like we are likely to encounter the UX of "Help" more and more. Just like a bad UI experience, the help experience can leave the user with a giant floating question mark above their head. Consider adding in special testing in your formative testing efforts to help safeguard against a bad "Help" experience.
You can find the above mentioned book along with many other great reference texts on the User Experience Reading List.