https://bugs.winehq.org/show_bug.cgi?id=39387
--- Comment #3 from Ken Thomases ken@codeweavers.com --- (In reply to Nikolay Sivov from comment #2)
Rendering is done by freetype on and doesn't depend on a platform font rendering. However it's certainly possible you're not using same version/build flags for freetype on both systems. Is that possible your macos lib is old or built with some features disabled?
Well, the other source of potential differences is with the font itself. OS X comes with several faces of Verdana. According to a +font log, the system Verdana is preferred over the one from Core Fonts because the system one has a higher version (5028f vs. 10000).
I'm seeing results very similar to the Corrupted "W" screenshot using the FreeType from XQuartz and the libcxfreetype from a trunk CrossOver build.
Indeed, if I use /Applications/Font Book.app to disable the system Verdana, then Wine uses the Verdana faces from Core Fonts and the Horn of the Abyss installer looks like WineBuG's Correct "W" screenshot. However, I'm not sure what's really correct. If I'm interpreting the +font log correctly, the whole string is supposed to be rendered bold.