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A couple of things I've noted over the years:

- Fields, or anything that uses fields: They're completely broken. They only seem to function in straight-forward case. For e.g: it's very easy for sequences to completely go off whack.

- File comparisons: this feature can only tolerate up to a certain number of pages. It will crash and burn for large documents. I sometimes wonder why this is even offered!

- Formatting: No matter how carefully paragraph spacing etc. is controlled there are always instances where things won't work as intended. A good example is cover pages.

- Hanging and freezing on large documents while Word figures out how to render them.

- Font rendering: it's never great. It never looks the same as what it would on a printer (irrespective of the printer). The Mac version does a decent job, but the Windows version, even with ClearType configured, is not great.

- Lastly, my biggest issue: feature incompatibilities between the versions of Word available on Mac and Windows. The Mac version (the latest O365) release doesn't have a lot of advanced features that are available on Windows such as document signing and style breaks.



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