So I'm an amateur type geek—no doubt a side-effect of writing for a living. Since I do text (rather than graphic) layouts, I'm more interested in text faces and book design than display headers and splashy type.
Font-creating programs can be quite, ah, expensive. Fortunately, there are some decent cheap ones—which may not have all the features but are good enough for getting started: Softy (£15/US$25, doesn't hint; here's a tutorial) and Font Creator ($79). TrueType Typography might be useful, with much nifty information about TrueType and how it works. Also notice Microsoft's TrueType Developer Page.
On the shaping of glyphs, helpful sites include tours of comparative letter forms at typoGraphic and Counterspace, and these three basic tutorials. Typographica, Typographer, and Microsoft are good for type design news, TypoWiki has How-Tos, and the forums at Typophile can offer advice. You might also try Hildegard Korger's Handbook of Type and Lettering. Identifont and What the Font? can help train your eye for faces, in addition to usefully identifying type. For sideways thoughts on typeface design, look at Alphabet Soup and the Synthesis Machine, this essay on why