Resources and advice for teaching LaTeX
I'm going to address my answer the part of your question that had to do with “motivating interest”.
One way to sell LaTeX I think is to stress the potential benefits for the profession as a whole (and perhaps academia as a whole).
In the current economic situation, nearly all Universities are struggling financially, and library budgets have been hit particularly hard. Couple this with the fact that institutional subscription costs of Academic Journals published by the large academic presses are ridiculously high, and we have a huge problem.
The traditional workflow for a journal article would be composition in Word, then layout by the publisher in something like Adobe InDesign. Word is proprietary and expensive, and InDesign more so. But LaTeX generates output with comparable quality (--I actually prefer it--) using a format comprehensible to an intelligent end-user, and its completely free to use and open source.
Point to Philosopher's Imprint as a Success Story. It's not uncommon to hear philosophers put down the quality of online journals, and put down this model. But this is a self-fulfilling prophecy, and Philosopher's Imprint is a huge exception. It's published by the University of Michigan, has a rock solid reputation for quality, and is completely open access to anyone with a web connection. It's no coincidence that they're using LaTeX for typesetting; it saves them thousands of dollars a year in licensing fees. Their document class is on CTAN; stress how easy it would be if all journals had their templates and bibliography styles there too.
Imagine the potential savings to the discipline as a whole if this model caught on (not to mention speed in a discipline in which it can take well over a year for something to appear in print).
And while maybe I'm thinking overly optimistically, this could be a good segue into discussion of the benefits of open source generally, and the philosophy behind it (which I think would appeal to many, if not all philosophers, even those who aren't super-tech savvy). Stress that LaTeX is more cross-platform than Word, and that it frees us from the mercy of Microsoft and Adobe's pricing policies.
Stress the relief from the upgrade treadmill. I think a lot of academics are still smarting over the transition from .doc to .docx and being more or less forced into upgrading to Word 2007 as a result. Stress that the LaTeX format has changed little in the past 20 years, and as a plain-text based open format, it has no proprietary secrets to hide. (I know Microsoft has taken steps to move towards making their XML specifications an open standard, but from I hear, they're not really sticking to it.) And when you do upgrade your LaTeX system, it doesn't mean a lot of new costs.
Stress the typographical quality, and show some comparisons. Show off some stuff from the TeX Showcase. Give a brief explanations of things such as paragraph-as-a-whole layout, pair and margin kerning, ligatures, hyphenation, vertical justification, math spacing, etc. I think a fair number of philosophers are nerdy enough to appreciate these.
UK-TUG has some resources at http://uk.tug.org/2010/07/30/training-day-a-success/, which were used as the basis for a training course. This was a single day event with a variety of needs from users: physics, chemistry, linguistics, computing, etc.
I have no idea what philosophers need from a text processor. The painless handling of references (both inside the document and to the bibliography) maybe? The question ”Most significant reasons that led us to (La)TeX” does list lots of good motivations. You could also impress them with http://people.umass.edu/klement/tlp/ (especially generating a index like this is probably rather painful in Word).