I won't get into a debate regarding UI development, except to say that every piece of software we have ever shipped began life as a template app from Microsoft and represented the closest thing to a standard at the time. The use of an About item for versions is still a very common approach, and when apps are dialog-centric and do not have menus, it was a very common thing to use the icon for the About. I doubt that consumer apps have as strong a dependence on versions as technical apps, which may account for versions not being at the top. We've tried to do better with Do-more because there are so many possible versions between firmware, software, and projects, which becomes much worse when you start migrating and improving the product as we have.
As for the H2-CTRIO stuff on our website, yes, I can see how you might have been misled. I will also gently point out that nothing there mentioned H2-CTRIO2. All of that was written when we re-defined the register set of the original CTRIO to enhance the product...and offered free upgrades and forward compatibility to our users. Choosing not to do such things is generally easier, but isn't the way we roll at Host. If I have to deal with the occasional pissed off customer because we continue to improve our products, I'll gladly accept the beating. We have learned some related lessons with firmware versioning since doing Do-more, and all Do-more firmware now uses the Do-more technology version as its major/minor version. The new platform will start with 2.0, since that will be the Do-more Technology Version it supports initially.
Final thought: As a user of technical software myself, I well understand the concerns about upgrading (don't get me started on Altera's Quartus) and I tend to resist upgrading until I absolutely need to. I get that. Seriously. I will also say that except for relatively rare cases (that we try to release quick patches for), new versions of Host software are always better, and if you ever find yourself struggling with something like the recent CtrioWB unpleasantness, it is likely related to your software being old. When in doubt...upgrade. We've made that even easier with DmD by allowing side-by-side installs with older versions.