It was very frustrating, because I noticed it just a few hours before the deadline. To work around of this bug, I had to insert manual page breaks (mostly randomly), and I had to make the vertical margins of the TOC pages smaller.
LaTeX has always generated the correct numbers in the last 25 years I've been using it. And if I got something unexpected, I was able to fix it for good (without document-specific hacks such as manual page breaks) by adding some macro calls. With LibreOffice and Microsoft Office, getting such a fix ready in 1 hour is hopeless for me, so I'll either miss the deadline or I hand in something incorrect and unprofessional.
Also: LibreOffice doesn't support character formatting (of a few words only) in the ToC. LibreOffice doesn't support omitting a few select sections from the ToC. LaTeX supports both.
In practice, Markdown is better than either for documentation that isn't printed. It's easier to edit, can be viewed with a plain text editor, and has a minimal learning curve.
No, it doesn't work well even if you know what you're doing. It's much better than when blindly trying to hack your way through, but there are still so many weird quirks it does which you always have to spend a lot of time on.
If only there was a way to create a Word document that forbids manual formatting it could actually be usable.
Well, I had to re-encode my documents twice in that time, once to isolatin1, and once to Unicode, because I was writing in Spanish and German. But it was actually fun to figure how to make that translation happen completely automated and happen in a few seconds.
Furthermore, our documents can't be written in LaTeX because half the people responsible for maintaining them come from a non-technical background with no experience in programming. No, we are not going to inflict a WYSIWYG LaTeX editor -- all of which are far less usable than Word -- on people just because some technical people want to pretend they're programming.
Nevertheless, our CS interns invariably say, "Why don't we use LaTeX for this documentation?" I understand why they want to. They use LaTeX for all their papers. However, it is inappropriate in our situation and has gotten to be a rather irritating question.
Yet you seem happy to prescribe your (extremely limited) views on everyone else without knowing their situation.
Good for you if all your documentation requirements are trivial, and I'm sorry to hear that your team cannot cope with trivial software installs or simple markup. Maybe the problems lie not with LaTeX...