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I suspect the differences is rendering is due to your .otf being Postscript-flavoured and your .woff TrueType-flavoured. They are also too small to render clearly with so much detail.
Hello and thank you for your interest!
As far as i know both files are Postscript, sfnt2woff exports Postscript as well as fontsquirrel.com. The renderer is Firefox 19.0.
I am rethinking my approach to shading with other methods, it was an interesting test but all round inefficient approach. I have found a new way by using CSS in the mix!
Yes, sfnt2woff can export Postscript, but Fontsquirrel does not. If you do intend to make icons this small, you’ll benefit from much more simplied shapes, TrueType outlines and hinting instructions. And yes, shading is better done with CSS.
And here are the results!
Updating the larger sets with this technique. http://dribbble.com/shots/968061-SF-W-I-P-32px-WOFF-with-CSS-Shading?lis...