Stabsalot

Race: Wood Elf
Class: Rogue(Assassin) 3/Ranger 3(Gloom Stalker)
       Rogue(Assassin) 3/Ranger 3(Gloom Stalker)/Monk(Shadow) 6/Fighter(Battlemaster) 3
       Rogue(Assassin) 4/Ranger 4(Gloom Stalker)/Monk(Shadow) 8/Fighter(Battlemaster) 4
       
Background: Charlatan
Speaks: Common, Elven, Thieves Cant, one other


Str 08                          = 08(+1)
Dex 15 +2[Elf] +1[Feat] +2[ASI] = 20(+5)
Con 10                          = 10(+0)
Int 14                          = 14(+2)
Wis 13 +1[Elf] +6[ASI]          = 20(+5)
Cha 12                          = 12(+1)

Stats
Hit Die: 8+2d8+3d10+6d8+3d10
Max HP: 100
Speed: 50 ft (+10 ft. first round of combat)
Initiative: +10 = Dex+Wis
Proficiency: +6
Armor Class: 20(10+Dex+Wis)
Passive Perception: 21
Saves: Dex, Int
Skills: Deception(Back), Sleight of Hand(Back), Perception(Elf), Insight(Ranger), Acrobatics, Stealth, Investigation, Persuasion

Proficiencies:
Armor: Light armor, medium armor, shields
Weapons: Simple weapons, martial weapons
Tools: Thieves kit, Disguise kit, Forgery kit, Poisoner's kit, two other

Feats:
Rogue 4    - Elven Accuracy
Ranger 4   - Dex +2
Monk 4     - Wis +2 or Wis +1 & Con +1
Monk 8     - Wis +2 or Resilient(Con)
Fighter 4  - Wis +2 or Resilient(Wis)

Features
*Expertise(Stealth, Perception)
*Sneak Attack(2d6)
*Cunning Action
*Assassination 

*Favored Enemy(whatever)
*Natural Explorer
*Fighting Style(Dueling)
*Primeval Awareness
*Dread Ambusher
*Umbral Sight 

*Unarmored Defense
*Martial Arts(1d6; 6 Ki points)
*Deflect Missiles
*Slow Fall
*Extra Attack(1)
*Stunning Strike(DC 19)
*Ki-Empowered Strikes
*Shadow Step 

*Fighting Style(Archery)
*Second Wind(1d10+3)
*Action Surge
*Combat Superiority(4#1d8; DC 19; Menacing(Wis), Trip(Str), Riposte(AC))

*Keen Senses
*Mask of the Wild

Spells (DC 19, Spell attack +11)
Spells known: Absorb Elements, Hunter's Mark, Fog Cloud +Minor Illusion +Disguise Self
Spell slots: 1st Level(3) 
2 Ki each: Darkness, Darkvision, Pass Without Trace, Silence

The Stabsalot Surprise:
Set-up:
Note: starts to work at 14 lvl(Rogue 3/Ranger3/Monk 5/Fighter 3), after that only to-hit gets better
Have a shortsword
Cast Hunter's Mark on target
Achieve surprise
Expend 2 Ki and 4 Superiority dice 
Result: 
*two melee weapon attacks from Extra Attack
*two melee weapon attack from Dread Ambusher(for each Attack action)
*two unarmed strikes from Flurry of Blows
*two melee weapon attacks from Action Surge
*up to 4 attacks can be a Stunning Strike 

*all attacks are at with advantage
*all attacks are critical hits
*one melee weapon attack is a Sneak Attack
*four melee weapon attacks get Superiority Dice

1x 2d6(sword)+4d6(SA)+2d6(HM)+2d8(SupDie)+5(Dex)+2(Style)
2x 2d6(sword)+2d6(HM)+2d8(DA)+5(Dex)+2(Style)
3x 2d6(sword)+2d6(HM)+2d8(SupDie)+5(Dex)+2(Style)
2x 2d6(fist)+2d6(HM)+5(Dex)