Font Squirrel is the website that I originally used. Anyway, I just started completely over beginning with using a different font but I was editing the theme "Style.css" and not the JetPack Edit CSS. I got the different font to work fine. Then I switched to the font I want, worked fine. Moved the location of the font to a different folder, again worked fine. Then I used the original location of the font, again it worked fine.
Finally I tried to use JetPack Edit CSS and it failed yet again. So I messed with the url link to a bunch of different things and none of them work. For example:
- ../../uploads/2013/12/typewriter.eot
- wp-content/uploads/2013/12/typewriter.eot
- blog/wp-content/uploads/2013/12/typewriter.eot
and others, but I think those three are the most likely.
I still think you have a coding issue.