Dagger Master Feat

Heh, not going that route actually. I am going Way of the Open Hand, better fits the character as he was in 3.5. Had him has Swashbuckler/Fighter/Invisible Blade. Much more a nimble thug that likes knives than hiding or sneak attack.

That works too, I suppose. The monk for 5e is a lot of fun. Get the mobile feat, if you can, for extra shenanigans.
 

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Surgical Strike [ By studying anatomy you know where to aim to do the most damage. ]
- Finness weapons have a crit range of 19-20.
- If you land a critical with a dagger you may add your wisdom modifier to the damage when attacking a humanoid target (wisdom is the same attribute as medicine)
- Think it needs something small more to make it balanced. Maybe: You have advantage on medicine rolls. (too good?)

Feats are supposed to have multiple uses, like crossbow expert can be used with ranged spells in melee. So here I chose to make the crit range increase not be specific to daggers.
The increased crit range does overlap with the champion thing but that's fine, not all feats are viable for all classes, a fighter with weapon master is quite pointless.

Could also base it off the Sharpshooter or Great Weapon Master feats to get
- Before you make an attack with a finess weapon you can choose to take a -5 penalty to hit for a +10 to the attacks damage.
This would make daggers very interesting since you get the damage from shaprshooter and great weapon fighter in the same weapon. (though it has been confirmed that daggers can use the sharpshooter damage increase)
 
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Surgical Strike [ By studying anatomy you know where to aim to do the most damage. ]
- Finness weapons have a crit range of 19-20.

How does this work with the Champion?

- If you land a critical with a dagger you may add your wisdom modifier to the damage when attacking a humanoid target (wisdom is the same attribute as medicine)

Instead of or in addition to Dex / Str?
 

It doesn't stack with Champion. Things not stacking isn't something uncommon. For example you might as a Warlock pick the crossbow expert to be able to cast eldritch blast in melee ignored the other 2/3rds of the feat (ignoring loading and getting an extra shot with hand crossbows).

And it would be in addition to your str/dex modifier. Could make it into a choise between int or wis instead, this would allow you to synergize with arcane trickster aswell.
 

"•You deal 2d4 damage with daggers rather than the normal 1d4."

This is roughly similar to the ability to use non-light weapons granted by the Dual Wielder feat. 2d4 damage is only half a pip away from the 1d8 damage a rapier would grant you, and is otherwise identical (they are both piercing, finesse weapons).

"•You gain a +1 to AC when fighting with a dagger in each hand"

This is also similar to the AC benefit granted by the Dual Wielder feat, though specialized slightly in that it only works with daggers.

"•You do not suffer disadvantage for long range dagger throws"

This is similar to the benefit gained from Sharpshooter, but only works with daggers, a mediocre ranged weapon.


On balance, I'd say these benefits are not out of line when compared to the Dual Wielder feat.

Aside from the previously mentioned issue of this feat stacking with Dual Wielder, I'd caution you to avoid too much specialization as a balancing factor. One of the things that caused 3rd edition to get out of hand was the fact that specialization was used as a way to balance abilities; it resulted in the scenario where you were especially good at the things you wanted to do, and especially bad at the things you'd never do anyways.
 

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