Mistwell
Crusty Old Meatwad
This doesn't mesh with experience or with the published adventures. When encounters in a city are part of an adventure it very often requires many many skill checks between rests. A chase scene, an interrogation, an investigation scene, it would be far more common for a half dozen checks instead of just one or two. 5e doesn't have skill challenges like 4e but it often simulates them with many checks from several PCs.That would require multiple checks between short rests to be relevant. Which is reasonable in a dungeon, but not when the party is out and about in a city or wilderness. It's just a free better Expertise until lv17 on any check.
But again, fundamentally this entire discussion is silly. They're not even gathering data on the rogue, and it scored very high. This whole thing is a moot point.