Wondering, has anyone ever had any problems with compatibility, user complaints, or broken functionality by having "unconventional" styles in a single family all nested under one family name?
What I mean by "unconventional" are those styles that don't fit the typical weight or width conventions: Light, Bold, Italic or Oblique, Condensed, etc.
My case is that I'd like to nest styles like (FamilyName) Outline and (FamilyName) Shadow for a display family all with the same family... basically so it's just one family with the style dropdown displaying all of the "unconventional" style together—instead of breaking out into unique, but related families, e.g. FamilyName Outline - Regular, FamilyName Shadow - Regular.
I find it to be cleaner and more organized in font menus (I know Word has some of it's own ways of handling this), but maybe there's a problem with it I'm not aware of?
So, for legacy Windows environments (including older versions of MS Office), you must use a family of no more than four members, Regular, Italic, Bold and Bold Italic being the only options. At least, if you want your font to work properly.
The open question is what you put in the font for more savvy environments. This is much more open-ended.
You may if you wish keep these sets of names the same as those required for Windows, so that no "family group" has more than four members, and you have oddities like family = "Glurbish Black" and style = "Regular".
Or, like most font developers today, you may use them in a typographically savvy way, so you have family = "Glurbish" and style = "Black" and the single Glurbish family may have 4, 6, 8 or 200 members, as needed.
This way simple programs like MS Office will have their legacy four-member families, and more savvy programs like Windows Notepad can utilize the preferred compact modern grouping. (Seriously. Even Word 2016 doesn't recognize multi-member families. Okay, on the other hand, Notepad is not the only savvy app, Adobe programs work like that, too).
Okay, I tested the above only with modern, though still moderately standard styles like "Semibold" and "Semilight". I don't know if Notepad can handle Outline and Shadow. I guess there has been some problem when I tried to use a "Mediaeval" style in InDesign.
Note: I don't recommend using non-ASCII characters in font names or styles. So Mediaeval is OK, but not Mediäval.