I am doing a similar thing for technical documentation, basically i want to recommend some docs at the end of each document. I wanted to use the same approach you outlined to generate labels for each document and thus easily find some “further reading” to recommend for each.

How big should my sample size be to be representative ? It’s a fairly large list of docs across several products and deployment options. I wanted to pick a number of docs per product. Maybe I’ll skip the steps 4/5 as I only need to repeat it occasionally once I labelled everything once