I have written quite a lor of work in LaTeX and I am still perplexed by floating images and I can never tell where floats (images, tables) will be or should be, because it always jumps randomly from page to page.
My roommate at college had a thesis with lots of images and tables and he basically gave up on LaTeX because of that.
Also, installing fonts to MS Word is trivial. Installing fonts to LaTeX ... well... not so. You need to use XeLaTeX. Which breaks some other things. I tried to use bibtex with xelatex, and started to do some weird issues, until I found out that the texlive packages in debian/ubuntu repos are outdated, so I had to uninstall them and install it again from the website, and then something else broke.
Meanwhile MS Word just works as it is. And you don't need to learn the weird table syntax. And the weird floating logic. And the difference between TeX, LaTeX, XeLaTeX, BibTex, Texlive.
Don't get me wrong, LaTeX is still the best document processor I know of, and I use it all the time. I'm just saying that the "separation of domains" idea is a bit of a fantasy.
After having read some of Edward Tufte's material, this struck me. I think the main point is: "make it legible" and (Tufte) "as informative as possible". If its not maximally aesthetically pleasing, then so be it.
EDIT: I apologize if this is trite, but I think that's really the whole philosophy of (La)TeX.
Markdown seems to be the best, but isn't exactly wonderful. I wouldn't ever try to convince everybody I know to use Markdown for everything instead of Word!