I think I've struck the font motherlode for $60
In my wanderings about the internet I found a program called Hi Logic Scanahand. It's a font maker ($60 price) which gives you a template (see attached image) which allows you place an image to turn into a font. So the idea is that you put stuff in the boxes provided and the program produces a font out of it. What you choose to put into the boxes can be hand drawn symbols, a new font made from art software or any image you choose - but bear in mind that a font's pixels are either black or transparent. Not like photoshop brushes which allow greyscale transparency.
If you combine this with a vector program (I use Serif Drawplus, but I'm sure Inkscape would be able to cope):: Edit actually a Raster would work too but not as precisely:: you can use your vector program to Frankenstein an existing font and produce a new one. Add to it a free font making program ( I use 'Typelight') and you can do fine edits (e.g. kerning) on the font you made with Scanhand.
Using Scanhand and a vector editor I was able to create a 'new' (i.e. Frankensteined) font in a couple of hours - if you haven't tried creating a font, this is an amazingly short period of time. I took an existing font into my vector editor and jazzed it up, stuck it in Scanhand and it created the font. I've tried to create fonts before using font creation software (which is vector editing using the pen tool) but I quickly realised it would take a lifetime or two to do.
Using (pay for) Scanhand / (free? if Inkscape can do what Drawplus does) vector software (and if you need it - I have not had to use it yet ) Free Font editing software you can:
Create handwritten fonts.
Create symbol fonts
Create adaptations of existing fonts (note copyright issues though)
I've attached my first try (sorry if it looks crappy but I was so excited about this I wanted to do it as quickly as possible) of a Frankensteined font and a symbol font.
I did want to use Wag's or Ramah's brushes as my first symbol font, but both rely on greyscale transparency (fonts are either utterly black or utterly transparent) so I grabbed a pen and drew some crappy symbols which I scanned in to make the font.
I'll post again tomorrow about how easy it is to do this with the right software. This is really a great find.
So, to Summarise:
You can make a new font within a day once you've populated the template with characters. You can easily make a symbol font from hand drawn work (see atatched)
See my initial crap example fonts attached.
Also attached are styles that I've done in Drawplus, (all variations of Times New Roman) some of which I can make into fonts using this method so I can share them with you. Fonts like 'barbed wire' which rely on colour would have to be done 'in program'