Kat - This is going to be an answer about font aesthetitics in general... not about mechanics... and maybe not the kind of answer you're looking for... I think that anyone really interested in fonts and typography needs to have a solid foundation in the history of the alphabet and the evolution of letterforms... and should probably have some hands-on experience in edged-pen italic calligraphy.
I don't know where you get that these days. I was lucky enough to study in college with a man named Lloyd Reynolds, who was largely responsible for the revival of italic calligraphy and the study of old letterforms. Lloyd pointed out the if you were going to learn to draw people, you'd be well advised to draw them from life rather than from reproductions in books.
He felt the same about letterforms... but how do you draw a letterform from life? We used edged pens (Osmiroid fountain pens), and we practiced loops and lines for months as we learned the rhythms of edged pen calligraphy, from which most Western letter forms evolved. We looked at old alphabets and medieval manuscripts. We tried to make letters as alive as possible.
Lloyd's book, which I'm not sure is still in print, I believe is called "An Introduction to Italic Calligraphy." I'm sure there are other books, now. This sounds old fashioned, I know, but the alphabet goes back several thousands of years... and our electronic tools now are so removed from the origins of writing that it's easy to forget how letters came about and why alphabets look the way they do.
I'm sure others on the boards here can supply a more modern perspective, but this is how I'd start anyway....
