What drives a poor reputation for the Rogue class?

[Sindeloke]

[interesting idea about a skill revamp]

Huh. The idea of things within your skill set just working certainly helps to resolve the "skills beg for permission, spells simply happen" dichotomy.

It does kind of exacerbate the difference between the skilled and unskilled on both ends, though. I definitely like any idea that makes people who are supposed to be good at a skill, actually good, but I also have a lot of respect for the design goal that anyone in the party, with or without proficiency, should feel like it's worth rolling to try something in most cases. Under the current system, in theory, you'll see checks between 5-10 that give the barbarian a good shot at passing a religion check or give the wizard reason to feel unsteady but not hilariously clumsy on a rocking boat. Not being able to set anything below 10 means you have to either say the rocking boat isn't a problem for anyone, or that the wizard is going to be on his butt for twice as many rounds as he would have otherwise.

So, as a force multiplier, the new Cunning Strike is a great start, but I'd go farther, using Skill Tricks to open up tactical opportunities that other classes could exploit.

There's, of course, a whole other conversation here, about how tactical the game actually allows you to be, given rules (or lack thereof) around weapon reach, elevation, movement, status effects, etc. But yeah things like trips, granting attacks, debuffing enemies, and the like are definitely a good area of potential development. Use that bonus action to throw a haste potion at a buddy, or stab someone with a blade coated in an elemental spider venom that causes cold vulnerability.

Oh, so the familiar isn't replacing the rogue's scouting ability.

You can't have it both ways, unfortunately. Either the rogue is doing a bunch of checks and disarming and extra stuff that the familiar isn't doing, and therefore taking up more time and making the party sit on their thumbs doing nothing, or the rogue is doing exactly what the familiar is doing, and therefore isn't bringing anything unique or impressive to the table.