I have written, illustrated, laid-out, and typeset three books. (I have not typeset books written by anyone else.)
In 1996, when I was polishing up my first book for publication, I invested several hundred dollars in a typeface (colloquially, font): Syntax, from Linotype.
By 2003, as I was polishing up my second book, I really really wanted one or two additional weights. Linotype by then had released a new version of Syntax (called, confusingly, Linotype Syntax, or LTSyntax). There was no upgrade option. I purchase a new licence outright, for USD 1200 (including all of the weights, and the small caps variants).
Around a year ago, I started the process of migrating to FrameMaker on Windows (under Parallels, under Mac OS X, on Mac Pro Intel hardware).
I had lots of difficulty in converting my typefaces, particularly Linotype Syntax, into a form useable on Windows. Font management on Windows is poor (in my opinion), and there ware major challenges in naming the font, its variations (roman, italic, bold, bold italic), its weights (light, regular, medium, bold, extra bold, heavy), and the small caps (SC) variant. A related problem was configuring Windows so that Adobe Illustrator EPS files (illustrations) would open both and print identically on the Mac side and the Windows side. Again, lots of naming issues – and not filenames, because font names are embedded within font files. Finally, to future-proof my workflow, I really wanted to convert from Type 1 to OTF format.
Around this time, Linotype released another version of the typeface, now called Syntax Next. So, I thought, the thing to do is to just buy it.
However, this turns out (a) to be a big cost (Linotype offers no upgrade from a previous version), and (b) not a complete solution anyway, because apparently Syntax Next has no small caps variant. Linotype may say, “Well, Charles, Syntax small caps didn’t sell very well, that’s why we didn’t port it to OTF for Syntax Next.” I would’t call it poor marketing, it’s deeper than that: I’d call it poor product definition. [There is now a Greek version, nice for me to have lambda, gamma, just USD 89 for the roman typeface. But: additional USD 89 for italics, USD 89 for bold, and USD 89 for bold italics! Sheesh! I guess Linotype would argue that you shouldn’t have to pay for variants that you don’t use, but it seems crazy that a typeface company would promote the idea that applying italics is a luxury.)
Email to Linotype is answered by front-line support staff who follow their scripts but are generally completely unhelpful. (Even for very carefully posed, simple questions, it is a surprise when a support rep is able to sensibly answer exactly the question that is asked.)
Rhetorical question: Why is Linotype unable to figure out that the company is in the software business?