What drives a poor reputation for the Rogue class?

[Skrum]

It's funny to me that the comparison is "Barbarian who is fighting with the best combat-boosting feat for their class and has both Rage and Reckless Attacks already active, which maximizes the benefit of said feat, which is already an outlier" vs. "a Rogue using a fighting style that favors safety over damage". Of course the Rogue's going to look bad with that comparison.

I'm also not surprised that optimizers, who tend to go for an interpretation of the game that heavily favors classes that can nova are down on the Rogue, the class that has no real ability to nova (outside of a couple subclasses). The thing is that the Rogue shines in fights where you aren't free to dump your resources, because it doesn't cost them anything to sneak attack someone in the face.

OK so in my first damage comparison, I gave rogue 18 dex and sharp shooter, the ranged counterpart to GWM. And it did LESS damage. Rogues only get 1 attack, so increasing the chance to miss that attack and not trigger their sneak attack makes them a bad candidate to use let's see, basically the only feat that can increase weapon damage in the game.

I also want to point out that my criticism of rogue damage is contextual: they don't do anything else. If rogue did exactly the damage it did now but could also tank - I'd like them more. If, more fitting to their class theme, they did the damage they did now but also had good CC options - I'd like them more. But they don't do either of those things. They have poor map presence; yes they can skirmish, but as a member of a team, they are bringing very little except damage. And if that's all they're doing, well the damage should be good! And it's...kinda not.

Finally, barb is not a nova class either. In fact, barb is also widely considered a bottom 3 class and suffers from a multitude of their own problems. The fact that rogue compares poorly to barb is not a good look for rogue.

Sure, it uses the loose-y goose-y-est part of the system, but Expert skills on a high-level Rogue should effectively be treated like low-grade superpowers by the party. Barring really extreme cases, the answer to whether or not the T3 Rogue with Acrobatics Expertise can do something acrobatic is an emphatic​ yes.

Absolutely, there's some version of the game where rogues' skills are a major boon and worth the build resources the class spends on being good at skill checks. But that's not 5e. Skills as a whole are grossly underbaked and thus just aren't that interesting or impactful. Thus the rogue, who is good at skills, gets shafted. Yes it's crappy. But that's unfortunately how the game was written.