My favourite class in DnD (as little as I get to play it) is the Rogue. I like being the sneaky character that fucks about and wriggles their way out of trouble if need be. Thing is, I find after a while they just become the “roll dice to win” sorta class, and by 11th level you don’t even really need to roll dice on ability checks you’re proficient with if you statted your character just right. So I’mma suggest 3 changes that I personally think would make the Rogue a bit more fun.
1. Change the Sneak Attack damage: Basically all you need to do as a Rogue when it comes to combat is sit at the back, and shoot enemies that stand within 5 foot of your friends. By 20th level, you can dish out up to 60 extra damage for free, or even up to 120 extra damage if you roll a critical... Kinda insane. Maybe scale the damage dice down to d4s (up to 40 extra damage, or up to 80 on a crit), or even change it so you gain an additional Sneak Attack damage dice every four levels, instead of two. 20th level Rogue pumping out up to 30 extra damage, or even 60 on a crit feels less like you’re a skinny artillery cannon.
2. Change the Reliable Talent feat to the Cautious feat (name is WIP): The Reliable Talent feat just feels idiotic to me. If you roll a 9 or less on an ability check you’re proficient with you just treat it as a 10. It takes the point out of rolling dice, since if you just take the Skilled feat and stat you’re character right, and you pretty much can’t fail. My thinking with the Cautious feat (once again the name is WIP bear with me) is that if your roll equals or is less than you’re proficiency bonus on an ability check you’re proficient in, you can choose to reroll it and must take the next result. It’s not perfect, and may slow the game down a bit, but at least you can assess your roll and use your wits (kinda the whole point of the Rogue) and choose whether you want to stick with it or risk a reroll.
3. Adjust the Stroke of Luck feat: I find this one kinda lack luster, and I feel you’d be better just multiclassing for your 20th level due the state of this feat. If you fail an attack roll you can choose to succeed, and if you fail an ability check you can choose to treat it as a natural 20, once per short or long rest. Really all I’d do with this is include saving throws, kinda like Legendary Resistance. You have 3 ways to use this feat now, but only once per short or long rest (might need some adjustment in case that’s a bit OP but ah well).