The cheapest and easiest way to add a hyphen to the entire font is with TypeTool from Fontlab: http://www.fontlab.com/font-editor/typetool/ It costs $99 and is fairly easy to use. In TypeTool simply open the font, add the hyphen, and export (only exports truetype fonts though). I'm unsure about the legal concerns. I've been wondering the same thing myself.

This depends on the foundry (or designer or whoever who owns the rights of the font). Based on my little experience with Dafont, I can tell you that every font comes with some kind of text who tells you if it is allowed or not (it is called EULA = End User License Agreement). If there is not such text, or if the text doesn’t talk about this, you can contact the author via email. Most of the times, he/she will allow you to make the change if you explain your situation.

Whether it's legal or not depends on the terms of the license. You can always e-mail the font designer and ask them. There's always an outside chance that they'll add the hyphen for you.

An alternative to TypeTool is FontForge (http://fontforge.sourceforge.net/), which is free, somewhat tricky to install (unless you happen to be on Linux), and not totally intuitive. The FontForge website includes detailed installation instructions and, once you get past that, tutorials, which you may not need for the task at hand. Adding a glyph is mostly a matter of drawing Bezier curves; beyond that, you just set the sidebearings and generate the font.

You may still decide that TypeTool is the right tool for you, but you should at least consider the alternatives. On the one hand, the effort required to install FontForge may not be worth it for a single hyphen; on the other hand, $99 is a lot to pay for a hyphen.

I guess a third option is to pay for a font that already contains the characters you need...

If you do decide to go with FontForge and happen to run into problems, send me a message and I'll do my best to help. I'm no expert, but I think I can handle adding a hyphen.

Another option: if you have a hyphen of some other font that you like, you can make a Find & Replace search in your document.

Is there no way to move to a quality font? It will save you a lot of heartache in the long run.

With my somewhat limited experience, I've to say that using fonts from Dafont can get very messy down the road. It's not the first time I see this problem happen with accents, punctuation or even numbers. In one occasion, one of my partners used a font from Dafont and after finishing the job he was going to export a PDF (from InDesing). The font didn't allow embedding so he had to change the font, the text reflowed and he had to redo all of the text fitting. The funny part is that this typography was advertised as "free". Sometimes paying for a good font or downloading one free but better will pay itself several times when you start to work.

If you tell us what font you're using I might be able to help you further. Some of the fonts in that page are public domain so editing permission is not needed.

Regards.

Thanks so much for everyone's responses and ideas they were all very helpful. I am going to switch to a better quality font, deep down I knew this needed to happen, but I was just resisting and hoping for a quicker fix haha. Thanks again.

Happy to suggest alternatives if you can show us what you're using.

Oh thanks so much Stephen, I actually already replaced it though, but thanks for bringing me down to earth on the DaFont thing, you were right. If any of you have the time I could use some help on another handwriting font I am trying to find. I started a new thread: http://typophile.com/node/62825

Thanks everyone.

@amillerbrown: TypeTool can generate other formats than just TrueType: