Oh thank you, I didn't know that was referred to as "observability" I thought it was just logging. This article from Etsy's engineering blog [1] was part of the inspiration for this question. Funnily enough when I googled "Etsy engineering logging" the 5th result was for a position on Etsy's observability team.
[1] https://codeascraft.com/2011/02/15/measure-anything-measure-...