It might or might not be notable that the growth of that tech team included, one year later, hiring Larry Wall[2].
Given that, I'm not sure how to apply 'if Craigslist doesn't need it, I probably don't' as a general principle....
[1] https://www.slideshare.net/jzawodn/living-with-sql-and-nosql... [2] http://blog.craigslist.org/2013/10/15/artist-formerly-known/
They are no FB, but they're bigger than almost anything else on the web [0]. I doubt most people will build anything bigger in their careers. I certainly won't.
A huge caveat might be app features. Clearly running something like travelocity could require more pieces, and something like a BI app in a fortune 100 company would have many more connectors to data sources. But in general, they've done pretty well using only newer versions of what worked way back in 1999, and to me, that's just incredible.
My take is simple - if Craigslist doesn't need it, then I probably don't either. (I may want it, but that's different).
Definitely not perfect, but it works for me. Obviously more/better guideposts would make this a much better yardstick.