Oh yes, Rogue/Gloomstalker is an especially lovely combination, extra movement speed in the first round, invisible to creatures with dark vision while in darkness allowing you to back off and hide. Personally I love it with Swashbuckler (Dex, cha AND Wis to initiative? Yes please! Along with dudes you hit not being able to opportunity attack you, bonus action to hide in shadow then get advantage on the next turn is ridiculous) but considering the synergy with the wisdom abilities on Inquisitive it could easily work too.<br/><br/>It also works thematically, a member of the city watch learning to hide in dark places over time is really neat