You should look into LatexMk[0].
Oh, that's so true. I've spend far to many hours trying to help debug LaTeX code from friends and coworkers.
I'd give Office users that MS Office is easier to use if you want to write one page of plain text without anything else but above that Office is just a huge pain in the a... But the biggest problem I have with Office isn't whether it's hard to use or not but that the text it produces is simply ugly. Especially so if you have to work between different versions of MS Office and maybe even an OO user within the loop. (That would than probably be me...) The text layout MS Office produces is simply hideous.
There are shittons of templates.
The error messages suck though, that's true.
EDIT: nevermind, I didn't know Latexmk is a thing and is popular.
I now use rubber[0] to avoid this. I especially like that it has a --clean option :)
Which is always, because defaults are ugly as hell. Might work for math papers, but not much else.
My only real issue with LaTeX though is its error reporting, which is less readable than C++ template metaprogramming fails, and the fact you have to compile the same file $magic times in a row to get a stable render.