i.e. just take a smart undergrad CS major and record their screen (& audio) while they try to figure out how to use it. I think this would definitely turn up some tasks within it that are way harder than they need to be. Do people really feel confident that learning git is a smooth process, not involving a lot of swearing?
The answer you mostly hear when complaining about programming tools is that you need to toughen up - yet startups are founded on the idea of not doing this to their clients. Making processes super easy for clients is a good thing, and we should gather information, find the common problem spots, and fix them for our own tools! We shouldn't just keep insisting that the customer (programmers) needs to toughen up and learn (as the default answer, anyway; some things really are hard)
Why isn't there user feedback tool for man pages, where it asks "Was this information helpful to you?" every time you use a man page? I bet the success rate would be pretty low.
In general why isn't there any information about which man pages are good and which are terrible? They just seem frozen in time. Compared to the analytics startups get about their customers, info about man pages is nonexistent. Yet there are probably ones out there which would be rated "useless" 99% of the time, and have been for 10+ years with no change.