I've written two thesis in Latex and a small 100 page book in Word.
Word 2000 performed wonderfully. I had no problems with references or images shifting around, no strange errors, nothing. Bibliography sucked, but in general it was a pleasure to work with.
Word 365, on the other hand, is something I have to force to do what I want again and again. It is built in such a way that doing things cleanly and error-free is difficult and much less obvious than in Word 2000. Even standard tools like image anchors, which worked nicely in 2k, are not reliable anymore. I got the feeling that this is due to automatisms aimed at casual users.