FormerlyHemlock
Hero
I assume this advice only applies once you get the "take 10" ability?
It may just be the way I roll, but scouting out stealthed was fairly hit or miss for my rogue. 20% chance of failure is no big deal on an attack roll, but when it's on a "potentially trigger another combat and get jumped when your party is 2-3 rounds away" it's less good.
Though thankfully Cunning Action means that if I do win initiative I can run away and lead a string of enemies to my party, hopefully. That did work out well at least once![]()
Shadow Monks are also fantastic at stealth and scouting. And the "lead the enemies back to where the party is waiting inside of a Leomund's Tiny Invulnerable Fortress" is great if you can make them follow you.