On the topic of the Assassin rogue subclass, and critical hits
One of the Assassin's class features in 5th edition grants an automatic critical hit against any creature you hit with an attack, as long as it is surprised by you. I can handle granting advantage against such a target easily with a custom condition called "Surprised", by giving the player a condition that checks for the Surprised condition. However, forcing an automatic critical hit appears to be more tricky... unless there is some hidden parameter I've missed. It's an edge-case so I'm assuming there just isn't an effect or parameter for it in the Effects system.
I expect someone could write an extension for it, but alas, that is beyond my ken.
I suppose I'll just have to remind my player to hold shift when rolling damage against surprised targets, eh? :)