Are Shadow Assassins proficient with Sawtooth Sabre?

Are Shadow Assassins proficient with Sawtooth Sabre?

In RAW, how proficient is the shadow assassin with the sawtooth sabre?

Weapon and Armor Proficiency
A shadow assassin is proficient in all simple weapons, all light weapons, as well as bolas, net, repeating crossbow (light only), shuriken, spiked chain, and whip. The shadow assassin is proficient with light armor and small shields, but not heavy shields or tower shields.

Sabre, Sawtoothed Category: [light] Proficiency: [exotic]
A sawtooth sabre may be used as a Martial Weapon (in which case it functions identically to a longsword).
If you have the Exotic Weapon Proficiency (sawtooth sabre) feat, for the purpose of two-weapon fighting you can treat it as a light melee weapon; for all other purposes, it is a one-handed melee weapon.

Here’s scenarios we’ve been discussing:

  1. SA can not wield SS proficiently, since the SS is an [exotic] weapon.
  2. SA can wield SS proficiently, but cannot use it as a [light] weapon due to lacking the Exotic Weapon Proficiency feat.
  3. SA can wield SS proficiently and as a light weapon, since the SS is a [light] weapon and SA have proficiency in "all light weapons".

Assassin’s Death Strike Critical?

This is a question regarding the double damage of the Assassin’s Death Strike.

Let’s say a 20th level rogue uses the Sneak attack feature on someone, it is a critical and it fails the CON save for Death Strike. Would the damage be an additional 40d6?

Follow up question. Say that the Rogue in question had purple worm poison on the weapon in which it made the attack. Would the both the critical and Death Strike apply to it, or only one?

Another follow up question: Say the Rogue was using a Giant Slayer Shortsword and the target was a giant. If the giant failed the DC for Death Strike and it was a critical hit, would the 2d6 damage dice be doubled or quadrupled?

Per RAW, does knowing Assassin’s Stance allow for feats that have “sneak attack” as a prerrequisite?

I’ve read that both Craven and Staggering Strike are very good feats for a Sneak Attack oriented swordsage, however, per RAW, I don’t think knowing Assassin’s Stance would accomplish the prerrequisite of being able to make sneak attacks, since it’s more of an "added" ability rather than a "natural" ability like, for example, the Rogue has. So, as the title says, would RAW allow that? It could easily be houseruled, however my DM is already giving me the stink eye by multiclassing into Swordsage.

Would swapping the Assassin’s Imposter feature for the Scout’s Ambush Master feature be unbalanced?

Inspired by this question: Would allowing the Rogue sub-class (Assassin) to benefit from Supreme Sneak be unbalanced?

The Assassin roguish archetype is considered by some to have very weak class features at levels 9 and 13. The linked question suggests replacing the Infiltration Expert feature with the Thief rogue’s Supreme Sneak feature, which I think fits thematically and mechanically, although a sneaky rogue with proficiency and Expertise in Stealth probably won’t really need it or notice the benefits that often.

In a campaign where the Assassin’s RAW features at levels 9 and 13 won’t really come into play, I like the idea of replacing one of them with Supreme Sneak as the linked question suggests, but that got me thinking: what about the 13th level feature, Imposter?

For reference, the Imposter feature description (PHB, p. 97):

At 13th level, you gain the ability to unerringly mimic another person’s speech, writing, and behavior. You must spend at least three hours studying these three components of the person’s behavior, listening to speech, examining handwriting, and observing mannerisms.

Your ruse is indiscernible to the casual observer. If a wary creature suspects something is amiss, you have advantage on any Charisma (Deception) check you make to avoid detection.

Naturally, the first place I looked to was the 13th level feature of the Thief rogue, but I don’t think Use Magic Device is appropriate because it doesn’t fit with the theme of being an assassin, and it’s also a defining feature of the Thief archetype, hardly the same as a feature about sneaking, which by comparison is quite generic.

So, I considered the other roguish archetypes, looking for something that seemed thematically appropriate, and found the Scout’s 13th level feature, Ambush Master. It sounds like something that fits the flavour of a stealthy assassin, without being too niche like Imposter.

The description of the Ambush Master feature (XGtE, p. 47):

Starting at 13th level, you excel at leading ambushes and acting first in a fight. You have advantage on initiative rolls. In addition, the first creature you hit during the first round of a combat becomes easier for you and others to strike; attack rolls against that target have advantage until the start of your next turn.

This feature seems to synergise well with Assassinate, especially the advantage to initiative rolls… but maybe it synergises with it a bit too well? It’s certainly a lot more combat oriented, and clearly makes the Assassin archetype stronger than RAW, but does it make it too much stronger?

Would swapping the Assassin’s Imposter feature for the Scout’s Ambush Master feature cause any major balance issues for an Assassin?

Does Assassin’s Death Strike double the Damage from Poison?

Let’s say you coat your weapon with poison transmitted by injury from DMG. As we know the damage from poison is not tied to attack roll but to a CON save so the damage dice are not doubled on crit. But how does it work with Death Strike? Should I double the damage rolled anyway?

The Death Strike feature states:

[…] When you attack and hit a creature that is surprised, it must make a Constitution saving throw (DC 8 + your Dexterity modifier + your proficiency bonus). On a failed save, double the damage of your attack against the creature.

Deflect Missile vs. Assassin’s poisoned weapons

I found this question on poisoned arrows and the Monk’s deflect missiles ability.

What I’m wondering about is slightly different. The Assassin has poisoned weapons which do half damage if the target passes a constitution saving throw. The question I linked to above concluded that you need to factor in the poison damage for deflect missiles as the rules state is for all of the damage dealt by the missile. But the Assassin’s poisoned weapons calls for a saving throw which, I’d expect, only apply if the crossbow bolt actually hits. Does the monk really need to make a CON save against the poison before determining whether they managed to deflect the bolt and not take any damage at all?

On a related note, what if the monk has reached level 10 in that class and becomes immune to poison damage? Do you calculate based on the damage the bolt would do to a normal creature? What if the monk somehow has resistance/immunity to piercing damage? Do you half/ignore the damage from the bolt for the deflect missiles roll?