The learning curve is steep at the start, gosh knows I've done or tried to do more than my share of silly things, and been patiently prodded back into success, or ignored until I puzzled it out on my own. North Seminars are a good way to learn, the Buoy racing was a good tutorial, and using Exp to monitor/route something like the Pacific cup a good exercise.
Any program that evolves over time tends to an interface that is inconsistent, compared to one that was "architected".
Be very glad of a single developer personality, and not dealing with gang hacking. Try to figure out how to use some of the Sailing instruments from their manuals; again would you rather have accuracy and precision, or nice documentation.
We have some home grown TCAD/database/analysis tools at work, where the menu logic depended on who did the development, it's very powerful, very confusing for the uninitiated, and damn near impossible to maintain.
Don't get started on CADENCE EDA tools or SAS data analysis patched together from acquisitions that almost work, some of the time.
Converting versions of large tools is a multi-year experiment and prove out. (Don't ask about French and Germans collaborating on A380 using different versions of CATIA) Wife works in Hospital IT dept, you don't want to hear their horror stories that pop up in testing version, mostly.
The price to smooth out the interface (which is already well known by the experienced base,) is not worth the opportunity cost of adding features and zapping bugs.
The recent addition of the WiFi interface to H5000 and potential to integrate race timer betwixt is a lot more valuable than a few hundred pages of documents that have a transient value.
Nick, thanks for your patience, if you get to SF I owe you a few bottles of "Lioness".