Designing Type by Karen Cheng
Type Tricks by Sofie Beier
Practical Font Design by David Bergsland - I already knew a lot about lettering and typefaces before I made my first type, but I didn't know how to use font design software. This book got me started within a day using FontLab (similar tools to other drawing programs and Adobe Illustrator). FontLab is one of the industry's main programs for making professional fonts.
Studying existing fonts will develop your design ability. If you're interested in historical book types, try books by Jerry Kelly and Robert Bringhurst. If you're interested in historical and modern types, try Paul Shaw and Paul McNeil. If you're interested in decorative display types, seek out A Visual History of Typefaces and Graphic Styles (2 vols, covering different time periods) and books on signwriting/signpainting/lettering and calligraphy.
Websites to be aware of:
I use FontLab and it's intuitive and you'd have no need of Illustrator. You can import your scan, draw the shape over it, and it's immediately type-able and exportable. I'm a traditional artist too and I understand the frustration with software that slows down what would otherwise be effortless by hand. I've not had any frustration with FontLab. When I bought FontLab it came with this e-book (I don't think it's sold by them nowadays) and I'd recommend reading it. It's a great introduction and after reading it, I was able to open the software for my first go, and produce meaningful results. I'm connected to a scanner and printer, so I can also print text samples (from within FontLab, without needing to export the font file), review the hardcopy, modify by hand, scan, import, repeat. The company provided good support (and good resources, which you need if you want to add OpenType features) but I've also had great support from the community at typedrawers.com/ Hope this helps!