Wow - this is extremely difficult, then suddenly extremely easy, then difficult again, then becomes extremely time consuming, and finally extremely satisfying.
Tiny bit of background first: I'm a freelance graphic designer - I'm ok at it. I have a bachelors in graphic design from St. Ambrose University. I think they have top notch professors and programs that challenge you and MAKE you learn new things (that's super valuable to me). For a short while, I studied Typography and of course with logo construction, there's usually a typographic element that goes along.
That background doesn't make me a Typography pro - but it means that I sort of know what I'm doing and what to pay attention to. It also helps that I'm a HUGE nerd when it comes to Type and Logo design (I'm considering getting "helvetica" tattooed on my arm - yeah, I'm one of THOSE guys).
I LOVE spending hours on a logo - carefully adjusting line weights, properly kerning words and taglines until everything is perfectly balanced. It's hard work and time consuming, but fun for me (weird, huh?)
There's not much else for me to say here. I think it's more valuable to show the work instead. It's exactly as difficult and frustrating as I thought it would be.
I hand wrote this alphabet several times (probably not enough actually) and then chose each letter from different places to create it. I purposely chose a couple wonky letters when better ones existed. I feel they give my font some flavor.
I scanned at 1200 dpi - live traced in Illustrator, then spent hours cleaning each letter up. I tested the alphabet with words - further cleaned up letters based on that. Some letters look good in one instance, but not another - it's the challenge to make it work in all instances. You almost have to make it invisible so the eye can scan it and understand. If it sticks out, your eyes will stop while your brain tries to understand and the story has to pause.
I'm using TypeTool for Mac to create the font. In creating a basic font, it's fairly simple to use. It was confusing at first, but after a day, I think I'm pretty comfortable with it and actually recommend it if you want to dabble in font creation. Check it out.
This isn't a perfect font, but it's not meant to be. I think I achieved an organic feel that I'm happy with and the bit of flavor feels like my own voice.