What drives a poor reputation for the Rogue class?

[Blatant Beast]

Already covered this; 1 feat gets you one expertise, compared to rogue who gets 4 of them for 0 feats.

The answer "4 is greater than one" is a bit jejune. The Expertise Ability is clearly subject to marginal utility. A Rogue's fourth selection of Expertise, is generally not worth as much as their prior picks, because those prior Expertise picks were spent on addressing needs and wants, and the fourth Expertise pick is probably just going wherever.

The fact that the 5e skills themselves have differing inherent utility also further exacerbates the marginal utility issue above. Expertise in Performance is just not as generally applicable as Expertise in Perception, for example.

A Rune Knight fighter, that wants to be the King of Grapplers, does not need 4 options for Expertise, they just need Expertise in Athletics. The fact that the Skill Expert Feat also grants a +1 to an ability score, makes the opportunity cost very low, (especially for a VHuman fighter, whom is receiving extra feats from both race and class).

A Circle of the Moon Druid, that has Expertise in Athletics, has garnered a huge boost to their Wildshaped Grappling ability.

Ludic, in a prior post, mentions that a Rogue's Expertise, often is either enabling "win more" dice rolls, ("Hey look, my stealth check was a 37 against the DC 10"), or just maintaining a level of parity in terms of performance, (a 10 wisdom Rogue with Expertise in Perception, is performing at around the same level as a 20 Wisdom Cleric with proficiency in Perception, before Reliable Talent). I also find this observation to be true.

We also have design artifacts in the system that throw skill usage off, even when dealing with Expertise and the Reliable Talent abilities. The Reliable Talent ability does not help with Passive Checks, only active checks. A Rogue that wishes to be the most perceptive person in the world, still needs to take the Observant Feat, to increase their Passive Perception.

If your Rogue with Expertise in Stealth is trying to streak across the court during a NBA game, or across the stage during a Taylor Swift concert, that rogue is going to be spotted, as they are visible.

A Rogue, trying to cross a bridge made of webbing, stealthily, likewise runs into the limitations of Expertise: it does not matter that the Rogue's Stealth check was an astronomically high number, a Giant Spider's Websense still defeats a Stealth Ability Check of 42.

At some point, even the Stealthiest Rogue, needs magic, to succeed....that is the system as designed.

I would argue, it should not be this way. An Ability check of 31 is the highest result a PC without Expertise can achieve when they have proficiency in a skill and a +5 ability score modifier. A roll higher than 31 either requires preternatural skill or magic.

A Rogue's Expertise, should have built into it's description, degrees of success for super high rolls.

To go back to the example of a Rogue trying to Stealthily cross a bridge made of webs; a Rogue whom rolls a Stealth Ability Check greater than 31, should be able to defeat Web Sense, for example. At the extremes, an ability roll over 31, is showing that extreme skill, is like magic itself, and should be able to do things that normally would be impossible.

Without, something like this, Expertise at high levels, often is just "win more", which is not particularly useful.