In reply to "Entry-Level" Webfonting:
@hrant
All depends on the nature of the font you're starting with. OT rasterizers are generally more forgiving than TT rasterizers so sometimes there's no avoiding having to tweak the outlines to make them more TT autohint-friendly.
Another option is ttfautohint. (There's Windows and 'Nix executables available but I'm not sure about Mac.) Does pretty well with bold outlines, especially those with a lot of straight lines. A work in progress.