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Disclaimer: This section represents the results of cursory net research by shaja, and deals with US laws only. Laws in other countries differ, of course. It should not be considered actual legal advice. :)
The question of whether it is legal in the US to redistribute bitmapped versions of copyrighted fonts (such as Ren'Py SFonts created from non-free TrueType or Postscript fonts) has a somewhat muddy answer.
From the comp.fonts faq: First, the short answer in the USA: Typefaces are not copyrightable; bitmapped fonts are not copyrightable, but scalable fonts are copyrightable.
So, it would definitely be illegal to redistribute (for example) the arial.ttf font file included with Microsoft Windows, which is a scalable font copyrighted by The Monotype Corporation.
The actual visual representation of the font itself - the typeface - is not covered by copyright, though. Thus, it seems that taking the rendered font output and using it as the basis of another font file does not infringe copyright.
The comp.fonts faq does not mention the specific situation of using the output of a standard os font renderer to create a new font, but it does quote an article with mention of a similar situation:
Note that the designs themselves are still not protected in the U.S. A plagiarist could print out large sized letters (say, one per page) on an Apple LaserWriter, using a copyrighted PostScript digital font, and then redigitize those letters by using a scanner or a font digitizing program and thus produce a new digital font without having copied the program or digital data, and thus without infringing the copyright on the font. The quality of the imitation font would usually be awful, but it wouldn't violate copyright. Of course, the plagiarist would usually need to rename the font to evade trademark infringement. [As I write these words, I have the guilty feeling that I have just provided a recipe for type rip-off, but others have obviously thought of just such a scheme--John Dvorak has even proposed something like it in one of his columns.]
So it seems that using a copyrighted font to create an SFont for use with Ren'Py is indeed legally permissable. Whether it is morally justifiable is another question. My recommendation is to use fonts that, if copyrighted, are licensed to specifically allow redistribution and modification.