Some of the problem lies within the Windows operating system itself. Just like MS Word, Windows insists on organzing font styles in groups of four. But the OS doesn't always do this well. And other applications may not be in agreement how to organize font styles either. This can create big problems when a type family has dozens or even more than a hundred styles. Some styles can go missing in the font menu or be cancelled out by another style.
Adobe's applications are better at handling really large type families. Some other rival graphics applications kind of stink at it. CorelDRAW (and its built-in font manager) is one example. It will work okay with some type super families and then fail with others, letting italic styles replace upright styles. I recently synced the Sztos family from Adobe Fonts; the family is just two variable font files, upright and italic. In CorelDRAW both styles get rendered as italic! Derp. To make matters worse CorelDRAW does a terrible job with type objects when exporting artwork in Illustrator format. When the AI file is opened in Illustrator all the type objects have glaring line spacing problems. You have to create a fresh Illustrator document, build new point type or area type objects in that file and then paste them into the Corel-generated AI file and then use the eyedropper tool to fix the bad type objects. But it's best to first re-save that Corel-generated AI file in Illustrator, close the application and then re-launch it. Otherwise various type families in Illustrator are going to come up with certain styles missing in Illustrator's font menu. You can't have CorelDRAW and Illustrator running at the same time either. I think Corel's font manager does something to affect other applications.
The fonts themselves can also be a problem. I've opened some problematic fonts in FontLab's TransType application. The app is a font converter, but it will visually show the font naming table of a selected type family. You'll see a grid with four font styles in each square. When a Bold-Italic weight is sitting alone in its own square it's clear there is a problem. Often another square will have 3 fonts and empty space where that orphaned style can be moved. I've tried using TransType to fix the problem with varying degrees of success. It works okay when converting simple Type 1 fonts to TrueType format. It doesn't work so well when trying to just re-save a more complex OpenType font in the same format. The font naming table issue gets fixed, but then some of the glyphs, such as fraction sets (numerator and denominator figures) get messed up.
I get the feeling a lot of typeface companies and typeface designers are unaware of these problems. I doubt Microsoft cares much about this issue either. I think the UI design in MS Office apps is awful. And they're block-headed enough to unleash terrible things such as Windows Ink into the OS.
In the meantime we're just stuck having to work around this garbage.
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