Great list. I remember being called in to look at software my company was thinking of buying, once... Only our finance/accounting people had looked at it so far. The thing barely worked. The desktop window kept flashing. Special characters were accepted and then broke the output. Extreme lack of features needed for the supposed goal.

I was able to find us an open-source / self-hosted solution that worked far better (bookstack). But I was amazed at how far the company selling the software got with us -- seems like most never get pushback, they just make sales by labeling themselves as fit-for-purpose regardless of whether or not they generally work.