In my opinion, the 2014 Assassin subclass is somewhat odd with respect to most (if not all) other subclasses. Why?
Most race, class, or sub-class feature are influenced by the character's own stats. Something might add an ability score to attack or damage. Something may allow the use of a feature an ability score time per day. Something may allow the use of a feature based on the character's level in that class. And so on. That means the character has some control over the feature. Increasing the corresponding ability score allows him/her to increase the benefit.
However, the assassin's assassinate, as written, seems to be an exception. The first part, getting advantage on attacks against foes that have not gone, follows that pattern. The assassin can increased DEX or get feats to increase bonus to initiative thus increasing the change of that benefit. However, the second part of the feature, the crits on damage, only apply when the enemy is surprised. This seems to refer to the actual 5E surprised game mechanics which requires the party's Stealth to have been greater than the Perception (or Passive Perception) of the party. Even if the GM is using Group Checks (where majority has to succeed) that still mean at least one or two other characters needs to succeed on their stealth checks to surprise the enemy. That means it is out of the assassin's hands. The assassin could have a stellar stealth but if the other 3 characters are fighters with jingling metal armor and no proficiency in stealth, then the party is unlikely to get surprise on the enemy...and the assassin will rarely get that auto crit benefit.
In my opinion, the class feature should be reworded to say "if the rogue is hidden". In such a case, the class feature is once again placed in control of the assassin because it is his/her stealth that matters. The alternative, which amounts to the same thing, is allow the rogue to break off form the group and be considered it own party for the combat. Essentially the loud party creates a distraction while the rogue sneaks around and cuts them form behind. Essentially that is the same as changing the wording to "hide" instead of "surprise" since the rogue's party of one means surprise will be determined (for his party of one) based on his/her single stealth action.
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In my opinion, the 2014 Assassin subclass is somewhat odd with respect to most (if not all) other subclasses. Why?
Most race, class, or sub-class feature are influenced by the character's own stats. Something might add an ability score to attack or damage. Something may allow the use of a feature an ability score time per day. Something may allow the use of a feature based on the character's level in that class. And so on. That means the character has some control over the feature. Increasing the corresponding ability score allows him/her to increase the benefit.
However, the assassin's assassinate, as written, seems to be an exception. The first part, getting advantage on attacks against foes that have not gone, follows that pattern. The assassin can increased DEX or get feats to increase bonus to initiative thus increasing the change of that benefit. However, the second part of the feature, the crits on damage, only apply when the enemy is surprised. This seems to refer to the actual 5E surprised game mechanics which requires the party's Stealth to have been greater than the Perception (or Passive Perception) of the party. Even if the GM is using Group Checks (where majority has to succeed) that still mean at least one or two other characters needs to succeed on their stealth checks to surprise the enemy. That means it is out of the assassin's hands. The assassin could have a stellar stealth but if the other 3 characters are fighters with jingling metal armor and no proficiency in stealth, then the party is unlikely to get surprise on the enemy...and the assassin will rarely get that auto crit benefit.
In my opinion, the class feature should be reworded to say "if the rogue is hidden". In such a case, the class feature is once again placed in control of the assassin because it is his/her stealth that matters. The alternative, which amounts to the same thing, is allow the rogue to break off form the group and be considered it own party for the combat. Essentially the loud party creates a distraction while the rogue sneaks around and cuts them form behind. Essentially that is the same as changing the wording to "hide" instead of "surprise" since the rogue's party of one means surprise will be determined (for his party of one) based on his/her single stealth action.