What drives a poor reputation for the Rogue class?

[strangebloke]

Something no one has thought to mention yet... but as much as the evil villain organization doesn't trust you, the PC, they also don't trust each other. They're all a bunch of self-serving back-stabbers when you get right down to it.

You know what a bunch of people who work together but don't trust each other aren't going to be surrounding themselves with? A bunch of mind readers and true seers.

You mean like, githyanki, drow, illithids, fiends, liches? ...all of which have mind reading or truesight or other divination present in the statblocks for creatures up and down their evil hierarchies? Evil orgs that don't trust each other are more likely to rely on magic to test their minions and allies.

But the point more generally is that pretending to be a random person who they've never met before might get you in the door, but that's about all its going to do as far as infiltration. Pretending to be a random evil swordsman might get you a job with the lich, but they're not going to tell some hireling everything about where their phylactery is stored. There's going to be like. Locks. Encrypted journals. Relationships you need to build. If you just want to get in the door, that's really just... not that hard.

The main advantage of this ability is maintaining a cover for a really long period to become a mole and build up to getting really deep access to stuff that's really protected. But this is not a style of play that's going to fly with the real humans who are also at the table with you and aren't built for this.