Mind you, I couldn't care less if she used Outlook over Apple Mail. Doesn't matter.
However, her use of _Pine_ indicates many things:
* Non-negligible tech expertise. She is comfortable with a terminal and confortable with an old (albeit powerful) email client WHICH DOES NOT DO HTML MAIL.
* Background: could be anything, but Pine usage is correlated with engineering and university backgrounds.
I could go on. The point is: she is no normal clueless CEO having secretaries printing out emails. And that's depressingly rare these days, even in SV.
A Time interview from August 1997 confirms that:
http://allaboutstevejobs.com/sayings/stevejobsinterviews/tim...
Also, in fairness, the circa 1997 Thinkpad was the best business machine on the market. Period. Macs had to catch up. The Macbook wasn't even a figment of anyone's imagination back then. The Powerbook 3400 (c. early 1997) was faster than the Thinkpad, but the productivity suite available at the time wasn't anything to write home about, let alone use for serious presentations.
All that is to say, I'm not as shocked on reading this as I guess I should be. From everything I've heard, Jobs only took dogfooding so far. If he didn't believe an internal product was the best for a given purpose, he didn't dogfood it. (I would be curious to know if he used Mail, for instance...)