I just got a copy of The academic Job Search Handbook (2008, 4th ed.) by Julia Miller Vick and Jennifer S. Furlong. Wow. I wish I'd known about this earlier.
Not only does it include a timetable for planning job searches, but it has examples of vitas, cover letters, teaching philosophies, etc. There are also discussions of the job interview, and strategies for job searching when your partner is also an academic. I haven't read the whole thing yet, and I realize that it is not tailored to our particular discipline, but it looks like a great way to get familiarized with the general process in a way that is not overly intimidating.
I ILLed it, as the on-campus copies apparently don't allow borrowing privileges. You can preview it at Google Books.
Have any of you come across this before and have any opinions about it before I dive completely in? As far as I know, there's not another book like this (though many online discussions of similar topics).