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 Arial is bad, thoughts on the history of serifs, and the non-Latin faces from the Yamada Language Center.
Warning: when it comes to freeware and shareware typefaces, you get what you pay for. It costs to get the Good Stuff, and for a good reason: a quality, readable text face requires a couple hundred detailed drawings by an expert (and that's just to get the glyphs).
Despite that, there are tasty morsels hidden in these collections for cheapskates: Fontastic, Font Fairy, the Font Foundry, dincFONTS, DaFont, Jeff's Fonts, Stuff Fonts, Pixel Fonts, Fontosaurus, typOasis, OldType, and places in these directories. Monospace Fonts has a specialized list, while Good Fonts has a collection of 300 free "essential fonts for designers." Phil's Fonts has a free font every month, and good prices on everything else.
Several professional type designers offer sharewares or freewares along with the purchasewares. These include Scriptorium (much nifty art type), Letterhead Fonts (old-fashioned display), Crazy Diamond (historical faces), LettError, Chank, and FontFont.
I've turned my writing into a face: (HCHand). This TrueType version (v0.9.8, 31.Mar.01) for Windows isn't quite ready for prime time: kerning is incomplete, glyphs aren't hinted (so it looks cruddy on screen if it isn't antialiased), and works best only when printed at 24 pt or so. Nonetheless, I'm offering it here as freeware.
One starting place is Fontsite, a cool 'zine with good print design advice; ITC's U&lc Online does the same for the web as well. The &Type section of the Design & Publishing Center has some good pointers. For general info, there's an Encyclopædia of Typography.