I completely agree. I mean Moodle was insanely popular at the time, but the IT guy who installed it had to go around teaching everyone how to use it - to the extent that there were multiple sessions booked in the auditorium where he demo’d it.

That’s fine, but relatively expensive when you consider that the IT guy’s time could have been better used elsewhere and that the IT department didn’t get any additional funding because they saved the university untold amounts of money that were provided by grants.

It’s also difficult to con alumni into donating for “Joe to do training on blah”... but donating to purchase the revolutionary new software from blah to increase admissions and donations while reducing labor is an easy sell.

That sounds like a business opportunity for the IT guy to develop a curriculum and sell it to other schools.

This seems like boring work that people might not be excited about doing for free. What about crowdfunding materials that will be distributed under and open license?

Yes, there is. Selling books, seminars, and certifications is very common in the Linux world.

But most of those are targeted to the IT side of things, aren't they?

I don't recall having seen much targeting end users.

It really depends on what you're looking for. I've found for popular applications there are usually tutorials on Youtube at the very least.