Outsourcing your webapp maintenance to Debian
It turns out that I'm not the only one who thought about this approach, which has been named "debops". The same day that my talk was announced on the DebConf website, someone emailed me saying that he had instituted the exact same rules at his company, which operates a large Django-based web application in the US and Russia. It was pretty impressive to read about a real business coming to the same conclusions and using the same approach (i.e. system libraries, deployment packages) as Libravatar.
Regardless of this though, I think there is a class of applications that are particularly well-suited for the approach we've just described. If a web application is not your full-time job and you want to minimize the amount of work required to keep it running, then it's a good investment to restrict your options and leverage the work of the Debian community to simplify your maintenance burden.
The second criterion I would look at is framework maturity. Given the 2-3 year release cycle of stable distributions, this approach is more likely to work with a mature framework like Django. After all, you probably wouldn't compile Apache from source, but until recently building Node.js from source was the preferred option as it was changing so quickly.
While it goes against conventional wisdom, relying on system libraries is a sustainable approach you should at least consider in your next project. After all, there is a real cost in bundling and keeping up with external dependencies.