Mistwell
Crusty Old Meatwad (he/him)
I am working on making a Dagger Thrower, and would like any helpful commentary, advice, changes, etc. that folks can think of.
This is the build so far, up to level 5. I chose human for the extra feat, though Halfling could work to use sneak behind a medium size ally instead of Skulker (I like Skulker more personally - hiding in shadows is more versitile). Cunning Action would not be used in the first round (you go into combat already hidden with two daggers in hand, and use your bonus action to throw that second dagger), but it could be used to get the heck out of there on round 2 (your foes were surprised on round 1 so didn't act) and prepare for another set of attacks. You don't have the Dual Wielder feat, so (depending on how you read the rules) you cannot draw two daggers each round and are stuck drawing just one per subsequent round. But really this guy is focused on assassinating his target on round one, and then moving on and hiding again to prepare for more attacks on round 3 if necessary, or returning to the party if you were scouting ahead and decided to assassinate a target you found.
Why Daggers? It's the only light (two weapon attack), finesse (dex instead of strength), thrown weapon (attacking from as much as a 60' range (sharpshooter) is much safer than melee range). The low base damage isn't important, because the Sharpshooter feat is adding +10 to damage (at -5 attack, but advantage from attacking while hidden basically is a wash with that), and Assasinate is making it a critical hit which doubles sneak attack damage in addition to base damage. Plus, daggers are cool (like fezzes).
By my calculations (see below), this guy at 3rd level (if he can hide without skulker) or 4th level (if he needs skulker to hide) does an average of 47 damage on that first round if both daggers hit, going up to 54 damage at level 5. That seems pretty darn good, for a guy with just a bunch of throwing daggers.
From there you can take more Rogue levels, or in the alternative take a level or two of fighter or ranger to get dual wielding, which adds your dex bonus to the off-hand dagger attack. Fighter comes with second wind at level 1, and action surge at level 2. Ranger comes with favored enemy tracking for more assassin theme, normal pace stealth movement when you're alone, and spellcasting that helps with the superb hunters mark spell (add another +1d6 damage to each dagger attack) and hail of thornes (burst 5' on your first hit of +1d10 damage (save for half)). Technically I suppose you could do both fighter 2 and ranger 2, picking up the Archery ability for +2 attack with each dagger. But I don't think that is necessarily worth it.

This is the build so far, up to level 5. I chose human for the extra feat, though Halfling could work to use sneak behind a medium size ally instead of Skulker (I like Skulker more personally - hiding in shadows is more versitile). Cunning Action would not be used in the first round (you go into combat already hidden with two daggers in hand, and use your bonus action to throw that second dagger), but it could be used to get the heck out of there on round 2 (your foes were surprised on round 1 so didn't act) and prepare for another set of attacks. You don't have the Dual Wielder feat, so (depending on how you read the rules) you cannot draw two daggers each round and are stuck drawing just one per subsequent round. But really this guy is focused on assassinating his target on round one, and then moving on and hiding again to prepare for more attacks on round 3 if necessary, or returning to the party if you were scouting ahead and decided to assassinate a target you found.
Why Daggers? It's the only light (two weapon attack), finesse (dex instead of strength), thrown weapon (attacking from as much as a 60' range (sharpshooter) is much safer than melee range). The low base damage isn't important, because the Sharpshooter feat is adding +10 to damage (at -5 attack, but advantage from attacking while hidden basically is a wash with that), and Assasinate is making it a critical hit which doubles sneak attack damage in addition to base damage. Plus, daggers are cool (like fezzes).
By my calculations (see below), this guy at 3rd level (if he can hide without skulker) or 4th level (if he needs skulker to hide) does an average of 47 damage on that first round if both daggers hit, going up to 54 damage at level 5. That seems pretty darn good, for a guy with just a bunch of throwing daggers.
From there you can take more Rogue levels, or in the alternative take a level or two of fighter or ranger to get dual wielding, which adds your dex bonus to the off-hand dagger attack. Fighter comes with second wind at level 1, and action surge at level 2. Ranger comes with favored enemy tracking for more assassin theme, normal pace stealth movement when you're alone, and spellcasting that helps with the superb hunters mark spell (add another +1d6 damage to each dagger attack) and hail of thornes (burst 5' on your first hit of +1d10 damage (save for half)). Technically I suppose you could do both fighter 2 and ranger 2, picking up the Archery ability for +2 attack with each dagger. But I don't think that is necessarily worth it.
