What you're saying surprises me because I got that information right out of the online wine manual in the referenced URL. But even if you're right, it doesn't seem to make a difference either way because things look the same both before and after using those .FON fonts.
The documentation is, unfortunately, frequently out of date. The font rendering in particular has changed several times over the years, but not the documentation.
The current version of Wine has a few built in replacements for fonts, and perhaps these are too small (it seems like there have been several complaints lately). But if external TrueType fonts are found, Wine should use those.
It seems as if wine (and Quicken) are already using the TT fonts that are being served up by my font server. At least that's the impression I got from the debug output I ran earlier. And the screen fonts all look identical to their real Windows counterparts *except* for those that I circled.
In general, if there are any TTF fonts in your Wine c:/windows/fonts directory, then Wine will render those fonts directly (using Freetype) rather that use the X font server. That assumes you have reasonably recent FreeType rendering. This is actually the best way to go; it tends to produce better results.
That said, I wonder if perhaps this is a more subtle problem. For example, here is an attachment from Quicken 2002 Deluxe. It would appear to me that "Update" is using the very same font as "Options". And even on your screen shot, the same font family appears to be used for "Options" and "Update/Send". It appears only the point size is different.
I wonder whether there is a fixed amount of space on the button, and if the width of the string is to long with the normal font point sizing, than it might chose a smaller point size. I wonder if other buttons, with shorter strings, are rendered with a larger font?
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