Well, ultimately it will be up to the DM of our group. Thankfully, that isn't my job! LOL
I am seeing this as another player at the table. I play a cleric/rogue/wizard, focused on using my rogue in pursuit of augmenting my divine and magical gifts. The character in our group is a rogue (with a couple levels of fighter for two-weapon fighting and action surge). He easily gets into a fight with another target already engaged with the fighter or barbarian in the group. He uses sneak attack every round because he his target is within 5 feet of an enemy (e.g. the party's fighter or barbarian). The extra 3d6 damage is easily matching the average damage of the fighter and barbarian, even though now get two attacks due to Extra Attack. I see it in the other players when the rogue out damages them. Especially since he went with the Assassin archetype, so on the first round he is devastating if he goes first. Oh, yeah, and he is also a half-orc so gets the savage attacker thing or whatever it is, adding another die to critical hits (which the assassinate feature is).
Typically, we see this... He has a good initiative, goes first. Moves to the target and gets to assassinate. This make the attack at advantage (gets to add +3d6 sneak attack) and a critical if he hits. When he hits, he is thus rolling 4d6 shortsword plus sneak attack, doubled to 8d6, plus 1d6 for savage half-orc, is 9d6 and plus 3 for Dexterity. Average damage is 34.5 points. Oh, and after that he still gets to roll his second weapon attack as well with the off-hand. While not as bad, it is still 3d6+3, for another 14 points on average.
The fighter and barbarian don't even come close to matching this typically, and for the rogue this isn't far-fetched or because he power-gamed the character. Even on the rounds without the assassinate, he still gets the 4d6+3 and 1d6+3, about 24 points if he hits both attacks.
Now, compare this to the fighter with a war pick and dueling style, plus extra attack. He does 1d8+6 twice, average 22. Significantly less on the first round, and about the same as the rogue after wards. Granted, he has more hp and a better AC, and another +1 to attack rolls because his Str is better than the rogue's Dex. I guess that is how he will have to accept he is superior to the rogue in combat. Still, I see it in his expression when the rogue is dominating the battlefield.
Now, wait a minute.
Assassinate only crits if the target is
surprised, and surprise something
the DM determines on an encounter-by-encounter basis. The target isn't automatically surprised just because they haven't acted yet; that only grants advantage and it only grants advantage to the Assassin. In that case, the Rogue should have less than a 10% chance of a crit even when rolling with advantage. The surprise-for-automatic-critical aspect of Assassinate comes up very rarely because
surprise is relatively rare. You can only get the full benefits of assassinate if you've surprised the target
and you act before the target (since surprise expires at the end of the target's first turn).
Here's how Jeremy Crawford explained surprise (p9):
Sage Advice Compendium said:
Does surprise happen outside the initiative order as a special surprise round?
No, here’s how surprise works.
The first step of any combat is this: the DM determines whether anyone in the combat is surprised (reread “Combat Step by Step” on page 189 of the Player’s Handbook). This determination happens only once during a fight and only at the beginning. In other words, once a fight starts, you can’t be surprised again, although a hidden foe can still gain the normal benefits from being unseen (see “Unseen Attackers and Targets” on page 194 of the Player’s Handbook).
To be surprised, you must be caught off guard, usually because you failed to notice foes being stealthy or you were startled by an enemy with a special ability, such as the gelatinous cube’s Transparent trait, that makes it exceptionally surprising. You can be surprised even if your companions aren’t, and you aren’t surprised if even one of your foes fails to catch you unawares.
If anyone is surprised, no actions are taken yet. First, initiative is rolled as normal. Then, the first round of combat starts, and the unsurprised combatants act in initiative order. A surprised creature can’t move or take an action or a reaction until its first turn ends (remember that being unable to take an action also means you can’t take a bonus action). In effect, a surprised creature skips its first turn in a fight. Once that turn ends, the creature is no longer surprised.
In short, activity in a combat is always ordered by initiative, whether or not someone is surprised, and after the first round of combat has passed, surprise is no longer a factor. You can still try to hide from your foes and gain the benefits conferred by being hidden, but you don’t deprive your foes of their turns when you do so.
That means when the Assassin beats an NPC's initiative and they're surprised, this is what happens:
Round 1: The target is surprised (critical hit) and has not taken a turn (advantage)
Round 2: The target is no longer surprised (no crit) and has not taken a turn (advantage)
Round 3: The target is no longer surprised (no crit) and has taken a turn (no advantage)
When the Assassin
does not beat an NPC's initiative and they're surprised, this is what happens:
Round 1: The target is no longer surprised (no crit) and has not taken a turn (advantage)
Round 2: The target is no longer surprised (no crit) and has taken a turn (no advantage)
Given that your Assassin only has +3 to Initiative at best (unless they took the Alert feat at level 4), I do not see how they're winning initiative so often.
Furthermore the PHB says this about Surprise:
PHB said:
The DM determines who might be surprised. If neither side tries to be stealthy, they automatically notice each other. Otherwise, the DM compares the Dexterity (Stealth) checks of anyone hiding with the passive Wisdom (Perception) score of each creature on the opposing side. Any character or monster that doesn't notice a threat is surprised at the start of the encounter.
So the question is: Exactly how good is your party at rolling for Stealth? Generally, if they hear anybody coming then the answer to the question, "are the NPCs surprised?" is, "no." If you've got a light source, that's also a pretty big giveaway. If you
haven't got a light source, then you're all at disadvantage to Perception checks
even if you have darkvision and you're probably not going to detect anybody hiding at all.
You're going to be the party that's surprised.
Secondly, how is the Assassin moving so quickly in the first round of every combat? Remember, both Cunning Action Dash and attacking with an off-hand weapon require a bonus action. Are you telling me that every encounter begins within 30 feet?
If every encounter begins with the NPCs surprised, and every encounter begins with the opponents within 30 feet, it's no wonder that the Assassin seems overpowered!