I think we all know that rogue in general needs a rework - the playstyle of all three specs is definitely lacking. I love the theme/fantasy of outlaw rogue especially - a swashbuckling pirate - HELL YEAH man, sign me up - but at the moment, it feels like utter crap to play.
A thousand weakauras to track buffs, finishers that you can barely feel, see, or hear, and abilities that just don’t make sense. The dispatch animation is laughable - heeeeeYA! AOE also shouldnt be just (another) dull buff. Blade flurry is so lazy. Make it flashy. Give us an actual ability.
Sinister strike? For a pirate? Really? - Even the icon is a dagger. At least make it “cutlass strike” or something. Just doesn’t vibe.
Roll the bones was a nice idea - but in all truth just feels horrendous to play. Constantly knowing you aren’t performing optimally unless you have 5 buff is the exact opposite of the dopamine surge us gamers need.
Keep the theme - roll the bones is a nice idea - but maybe turn it into a skill-based proc i.e. the proc is only up for 1 global. RtB procs, and maybe a random damaging ability lights up, press it fast enough and you get a huge blast of damage, or an agi/crit buff.
The cc abilities work great. Kidney, cheap shot, all super cool.
But I just dont feel like a pirate right now - and I really want to plunder your ships. Not have my screen constantly screaming “Bad - Reroll”. And seriously, sinster strike? 
Also, fact there isn’t an ability called “skull and crossbones” blows my mind. The spec pretty much writes itself guys…