I'm skeptical that using content-based filtering will make much of a difference at this stage. If I were ingesting a lot of articles from some external source(s), content-based filtering would definitely be necessary. But I think we'll get better results from manual curation. As of now, about ~90% of the essays in the database were submitted by me--so cold start shouldn't be a huge issue, at least for people who share my tastes.
But at some point, I'll definitely do some A/B tests with content-based filtering.