The documentation is, unfortunately, frequently out of date. The font rendering in particular has changed several times over the years, but not the documentation.
Ok. Too bad, but Ok.
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.
I'm pretty sure that Wine is seeing and using all of the fonts that my font server is throwing at it. But just to be safe, I copied all of my fonts, including the MS fonts, into c:/windows/fonts. It made no difference.
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?
I'm not sure, but I don't *think* button size is the factor. On that page I referenced, the leftmost circle is showing buggered fonts that are not in a button. I also noticed something else. On the "Online" page there are 4 different tabs - Transactions, Payments, Tansfers, Email - and every one of the buttons on all of those pages are equally buggered no matter how small or large the button is. However, after checking all of the other other pages and tabs in the whole program, I couldn't find any other instance of non-readable fonts. Just those in the "Online" section. And within that section there's a bunch of them.
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