Oh, ummm, ok.
Do you mind putting 3 levels of assassin rogue in the build? The initial damage surge will scare the hell out of an initial party, and makes the goodies REALLY take your guys seriously. It'll put them on the back foot and require a fair bit of team coordination to stop the bsfs going down. Which is what you want.
But anyway, here's a basic Shadow Monk/Warlock build. It's long.
Male Half-Elf Sailor Monk 9 / Warlock 3
Lawful Evil
Strength 8 (-1)
Dexterity 20 (+5)
Constitution 12 (+1)
Intelligence 8 (-1)
Wisdom 16 (+3)
Charisma 15 (+2)
Size: Medium
Height: 5' 4"
Weight: 145 lb
Skin:
Eyes:
Hair:
Maximum Hit Points: 75
Speed: 45 feet [monk]
Armor Class: 18 = 10 + 5 [dexterity] + 3 [monk wisdom]
Proficiency bonus: +4
Initiative modifier: + 5 = + 5 [dexterity]
Attack (handheld / thrown): + 3 = -1 [strength] + 4 [proficiency]
Attack (missile / finesse): + 9 = + 5 [dexterity] + 4 [proficiency]
Strength save: + 3 = -1 [strength] + 4 [proficiency]
Dexterity save: + 9 = + 5 [dexterity] + 4 [proficiency]
Constitution save: + 1 = + 1 [constitution]
Intelligence save: -1 = -1 [intelligence]
Wisdom save: + 3 = + 3 [wisdom]
Charisma save: + 2 = + 2 [charisma]
Insight (passive): 17 (22 with advantage)
Investigation (passive): 9 (14 with advantage)
Perception (passive): 17 (22 with advantage)
Carry: 120 lb maximum
For groups using the optional encumberance rules:
If carrying more than 40 lb, encumbered -- -10 on speed
If carrying more than 80 lb, heavily encumbered -- -20 on speed, disadvantage on ability checks, attack rolls, and saves involving strength, constitution, and/or dexterity
Languages: Common Elvish Orc
Unarmed strike [+9 to hit; 1d6+5 bludgeoning]
Club [+9 to hit; 1d4+5 bludgeoning, 3 lb, light]
4 Daggers [+9 to hit; 1d4+5 piercing, 1 lb, finesse, light, thrown (range 20/60)]
10 Darts [+9 to hit; 1d4+5 piercing, 1 lb each, finesse, thrown (range 30/120)]
Short Bow [+9 to hit; 1d6+5 piercing, 2 lb, ammunition (range 80, 320), two-handed]
2 Short Swords [+9 to hit; 1d6+5 piercing, 2 lb, finesse, light]
-------
Imp familiar Str 6 (-2) Dex 17 (+3) Con 13 (+1) Int 11 (+0) Wis 12 (+1) Cha 14 (+2) AC 13; HP 10; Speed 20, fly 40; 24 as rat; 20 fly 60 as raven; 20 climb 20 spider; deception ++4; insight +3; persuasion +4; stealth+5; resi cold, bludgeoning, piercing and slashing from nonsilvered nonmagical weapons, immune fire and poison, darkvision 120 feet unimpeded by magical darkness, pasive perception 11, speak infernal and common; advantage on saves vs spells; sting (bite in beast form), +5 to hit, 1d4+3 damage plus 3d6 poison, save vs constitution DC 11 for half damage
--------
Feats:
Skill Name/Key Ability/ Skill Modifier/Ability
Modifier
Acrobatics Dex 9 = +5 + 4
Animal Handling Wis 3 = +3
Arcana Int -1 = -1
Athletics Str 3 = -1 + 4
Deception Cha 2 = +2
History Int -1 = -1
Insight Wis 7 = +3 + 4
Intimidation Cha 6 = +2 + 4
Investigation Int -1 = -1
Medicine Wis 3 = +3
Nature Int -1 = -1
Perception Wis 7 = +3 + 4
Performance Cha 2 = +2
Persuasion Cha 2 = +2
Religion Int -1 = -1
Sleight of Hand Dex 5 = +5
Stealth Dex 9 = +5 + 4
Survival Wis 3 = +3
At warlock level 3, this character knows 2 warlock cantrips.
Mark this character's Warlock Cantrip(s) here:
Eldritch Blast
Minor Illusion
At warlock level 3, this character knows 4 warlock spells.
Choices may include this character's pact spell options.
Mark this character's First Level Warlock spells here:
Armor of Agathys
Burning Hands [pact spell]
Command [pact spell]
Hex
Mark this character's Second Level Warlock spells here:
Blindness / Deafness [pact spell]
Invisibility
Mirror Image
Scorching Ray [pact spell]
At warlock level 3, this character knows 2 warlock invocations.
Check this character's chosen invocations here.
Devil Sight
Voice of the Chain Master
This character is proficient with at least 1 artisan tool set(s). Check any artisan tools with which this character is proficient:
Alchemist's supplies
Half-Elf
All Half-Elves get +2 on charisma (already included).
This Half-Elf chose +1 on dexterity (already included).
This Half-Elf chose +1 on wisdom (already included).
Darkvision (see 60 feet black-and-white in pitch-dark)
Advantage on saves against being charmed; immune to magical sleep.
One extra language (already included).
Two extra skill proficiencies (already included).
Sailor
You can secure passage for yourself on a vessels and have contacts in the seafaring community.
If you were a pirate instead, your bad attitude can intimidate others.
In any case, this character knows how to sail a ship (water vessel) and can navigate.
Monk
You chose proficiency in a set of artisan tools.
You chose proficiency in a musical instrument.
Level 1: Unarmed strike damage 1d4
Level 1: Either strength or dexterity is used to calculate to hit and damage for unarmed strikes and monk weapons
Level 1: Unarmored defense -- if no armor or shield, add wisdom and dexterity bonuses to armor class
Level 2: Two ki points -- usable for flurry of blows, patient defense (dodge as a bonus action), step of the wind (disengage or dash as bonus action), ki points renew upon making a short rest. Afterward, ki points equal to monk level.
Level 2: Flurry of blows -- spend a ki point to make two additional unarmed attacks as a bonus action
Level 2: Patient defense-- spend a ki point to make a dodge action as a bonus on your turn
Level 2: Step of the wind -- spend a ki point to make a disengage or dash as a bonus action on your turn, double jump distance for that turn
Level 2: Unarmored movement -- add ten to speed if unarmored and no shield
Level 3: Deflect missiles
Level 4: Slow fall -- use your reaction to reduce falling damage by 5x monk level
Level 5: Extra attack
Level 5: Stunning strike -- critical hits may stun opponent to end of next turn
Level 5: Unarmed strike damage 1d6
Level 7: Evasion -- no damage if a dexterity save is made, half damage if failed
Level 7: Stillness of mind -- use your action to end charm or fear
Level 9: Move along vertical surfaces and over liquids normally
Shadow Monk (monastic tradition)
Level 3: Shadow Arts -- use ki to duplicate darkness, darkvision, pass without trace, silence; gain minor illusion.
Level 6: Shadow step -- from one shadow to another.
Warlock
The DC to resist your spells is 8 + proficiency bonus + your charisma modifier.
Level 1: One spell slot / short rest, slot level 1.
Level 2: Two spell slots / short rest.
Level 2: Two invocations known.
Level 3: Spells slots are level 2.
Fiendish patron (warlock)
Expanded list of available spells.
Level 1: Dark Ones Blessing -- on reducing enemy to 0 hp, gain temporary hp equal to yourcharisma modifier plus warlock level
Chain pact (warlock)
Level 3: Familiar becomes available
First Ability Score Improvement: +2 dexterity
Second Ability Score Improvement: +2 dexterity
Class HP rolled
Level 1: Monk 8
Level 2: Monk 5
Level 3: Monk 5
Level 4: Monk 5
Level 5: Monk 5
Level 6: Monk 5
Level 7: Monk 5
Level 8: Monk 5
Level 9: Monk 5
Level 10: Warlock 5
Level 11: Warlock 5
Level 12: Warlock 5
Equipment:
Acid vials x 2
Alchemist fire x 2
Arrows (quiver of 20) x 2
Antitoxin vials x 2
Backpack
Ball bearings (bag of 1000)
Caltrops (bag of 20)
Crowbar
Grappling hook
Hammer
Mess kit
Pitons (bag of 4) x 10
Rations (1 day) x 10
Rope (50', hempen) x 1
Rope (50', silk) x 1
Signet ring
Tinderbox
Torches x 10
Waterskins x 1
Alchemist supplies
Disguise kit
Forgery kit
Poisoner kit
Spell component pouch
Thieves' tools
A brass orb etched with strange runes
Plus points: Has shadow step, devil's sight, ki darkness, invisibility, hex etc. So the cover of darkness thing is cool, and can hit pretty hard against its hexed target.
Everyone comes with an Imp for more invisible shenanigans. Can sub out voice of the chainmaster if you want, but lets you proxy a proxied badguy. Also helps with anti-flight and "how did they know we were here?" complaints. Invisible imps, that's how.
Can run up walls and stuff with decent movement. Ki dash etc is possible. Can sub in expeditious retreat as a spell if movement becomes a problem, but competes for bonus punches and hexes.
Mirror image and armour of agathys desquishifies them a bit.
Patron can be changed to whatever. They're not actually meant to kill anyone.
Imps use shortbows too. They learnt how to from the shadow mooks. There's no reason for them not to be able to.
Could restat them as aarakroca if you're really worried about people just flying/running away.
Was a 27pt stat buy, incidentally.
I
personally think they're a bit weak. Give me assassin stab or BM die any day. Or a group of muhaha bards. But if you're set on shadow monklock, there it is. You can swap Charisma for Wisdom if you'd like, but mostly your spells are cast on yourself, so spell stats aren't a huge issue. As good as I can come up with for now anyway, with all the stuff you wanted.
