(response to edit)
> The classification problem is interesting though. I ended up with a long list of hundreds of topics. Most articles fall in two or more. There's also a sub-problem of clustering news by subject.
Yeah, certainly difficult. I'm doing it partially manually right now but also with fastText[1]. I'd like to switch completely to fastText soon though since more often than not the newsletters I add don't fit well with the checkbox categories on the landing page. Clustering the newsletters with fastText is pretty easy, but it might be hard to generate good tags for the landing page that match up with the clusters.