Sean,
As I'm sure you're aware, one comes across both ATCOs and pilots who are more able, and some who are less able, to take the 'big picture' into account.
I believe it is bad practice to enter into 'discussions' about mistakes on the R/T, as it can only distract the flight crew's attention, and anything that does that, especially outbound, if only a small amount, is potentially dangerous. You guys have enough to worry about without me passing critique!
We both can name colleagues who get annoyed sooner than others, over somewhat trivial matters, such as rolling slightly further down the runway than one might expect.
Keep up the good work with the CAP413!