Should I not try to help out the community with blog posts about my experience? Should we just cater to the experts?
I'm not sure what to tell you, except I fall squarely on the "old" side of that divide, having had to nurse Wordpress installations for nigh on 10 years now.
But every time -- every time -- an uncached Wordpress blog is linked to and dies with the famously unhelpful "Error establishing a database connection", somebody pops up to mention WP Supercache and/or W3 Total Cache.
Actually, if I have a pet peeve, it's that non-terrible caching isn't part of the Wordpress core. Probably breaks on gawdawfulhost.com or something, god forbid that 99.999% of the internet be better off from core architectural improvements when we could be working on the fifteenth new admin redesign!!1!
Edit: I realise now that you weren't talking about Wordpress and thus, my own pet obsession is clearly revealed.
My post was about middleman + s3 + cloudfront, however. I think this combination of tools isn't as well known and some people could benefit from knowing about them.
Out of curiousity, why middleman when you're already using Jekyll/Octopress?
(My dog in the static site generator fight is Nanoc, fwiw).