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Two thoughts: I'd love it if there was a website or book that discussed these big websites' workings in depth. Not just "here's this cool thing we built and an interview with the tech lead" but "here's how authors enter content" to "here are the problems we encountered while templating" to "here's what we wish we had built-into our software stack".

Secondly, a couple years ago I went directly to a "we are really good at Django" web host to try learning Django, but the amount of plumbing required was really annoying. I asked a Django-using acquaintance to send me his documentation on deploying Django-driven apps on this host, and I received a four-page Word document packed to the gunnels with instructions. :-/ I really want to try out Django though so I guess I'll swallow my pride.




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