D&D 5E Help Me With This "Shadow Boxer" Build (Just for Fun)

Bill Zebub

“It’s probably Matt Mercer’s fault.”
Basic Idea:
  • Shadow Monk, at least 6 levels
  • Crusher feat
  • Elven Accuracy feat
  • Champion Fighter, at least 3 levels
When you BAMF to a target you get Advantage on your next attack, which turns into Trivantage (Elven Accuracy) which gives you a 27% chance to crit (Champion Fighter), which would give you Trivantage on your 2nd attack (Crusher).

Additionally, if you use Stunning Strike and the target fails the saving throw, that's when you pop Action Surge and get a couple more hits with Trivantage.

Going 20 levels deep, what else would enhance this basic idea? From a fun standpoint, not just max DPR. (It's too bad fists don't count as finesse weapons because some Rogue would be perfect.)
 
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You are shadow-themed, have a feat dependent on generating advantage, already have access to action surge, and already need decent stats in both Dexterity and Wisdom. If there was ever a build begging for a Gloomstalker dip this is that build.

In a room with no light, against darkvision reliant enemies, burning your action surge and a ki point, you could make 8 tri-vantaged attacks on your first turn, often before anyone else even got to move.
 

Bill Zebub

“It’s probably Matt Mercer’s fault.”
You are shadow-themed, have a feat dependent on generating advantage, already have access to action surge, and already need decent stats in both Dexterity and Wisdom. If there was ever a build begging for a Gloomstalker dip this is that build.

In a room with no light, against darkvision reliant enemies, burning your action surge and a ki point, you could make 8 tri-vantaged attacks on your first turn, often before anyone else even got to move.

Sick.

Plus Hunter's Mark and Pass Without Trace.
 

Bill Zebub

“It’s probably Matt Mercer’s fault.”
How about this:

Shadow Monk 6
Champion 3 (action surge, blind fighting fighting style, and increased crit range)
Gloomstalker 7 (for ambush, some spells, and initiative bonus)
Assassin 3 (for expertise, cunning action, and assassinate)

Then probably spend last level on Fighter for feat and d10 hit die. Downside is that there are only 3 feats, which I guess are Elven Accuracy, Crusher, and...Mobility? Lucky?

I could give up 3 levels of Gloomstalker and get two more feats:

Shadow Monk 8 (add Evasion, Stillness of Mind, and a Feat)
Champion 4 (add a Feat)
Gloomstalker 4 (lose spell slots and initiative bonus)
Assassin 4 (add a Feat)
 
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To be clear the Gloomstalker gets their initiative bonus at level 3 (they get Wisdom save proficiency at level 7, which is also cool for a Monk not making it to Diamond Soul, but we can't have everything). I'd probably just go for the 3 of Gloomstalker (or 4 for an ASI), especially since Shadow Monk already can cast Pass Without a Trace with Ki (although not needing to spend it for that would be better, of course).

Assassin is cool, but really cool if you can bring yourself to occasionally use a shortsword of something that qualifies for sneak attack. With all the tri-vantaged attacks you are making you would rarely need to do it for more than the first attack before getting your extra 2d6. If you really couldn't bear to miss out on so many potential Crusher feat activation opportunities you could always use a sling and stone sometimes. It doesn't allow bonus action attacks, but there would be plenty of turns when you would be doing other things with your bonus action anyway.
 

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