So as a thought exercise, I levelled up both Shade-Of-the-Candle and Stars-At-Dusk to 20 to see how they compared both in a fight, and at their respective party roles. Here’s what I came up with:

SHADY: Bard (College of Swords) 6/Rogue (Swashbuckler) 14
AC 17, hp 167 (20d8+60), Spd 30, Initiative +11
Saves: Dex +11, Int +5, Wis +6
Multiattack (2/round); Crescent Moon: +12 to hit, 1d8+6 piercing +7d6 sneak attack; Cutlass (off-hand): +11 to hit, 1d6+5 slashing; Pistols: +11 to hit, 1d10+5 piercing
Acrobatics +17, Athletics +12, Deception +9, Intimidation +9, Investigation +11, Perception +12, Persuasion +15, Sleight of Hand +11, Stealth +17
Bardic Inspiration (d8, 3/short rest), Blade Flourish, Countercharm, Cunning Action, Distraction, Elegant Maneuver, Evasion, Fancy Footwork, Fighting Style (2-handed), Lucky (3 uses), Panache, Rakish Audacity, Reliable Talent, Uncanny Dodge
Spells: Charm Person, Cure Wounds, Enemies Abound, Enthrall, Healing Word, Hold Person, Mage Hand, Sleep, Thorn Whip, Thunderwave, Vicious Mockery

DUSK: Fighter (Champion) 15/Rogue (Swashbuckler*) 5
AC 20, hp 178 (5d8+15d10+60), Spd 30, Initiative +15
Saves: Dex +11, Int +6, Wis +8
Multiattack (3/round); Compelling Argument: +12 to hit (crit 18-20), 1d8+8 piercing +3d6 sneak attack; Longbow: +11 to hit, 1d8+5 piercing
Acrobatics +11, Athletics +12, Deception +8, Intimidation +8, Investigation +6, Perception +8, Sleight of Hand +8, Stealth +17
Action Surge (1/short rest), Alert, Cunning Action, Fancy Footwork, Indomitable, Second Wind, Uncanny Dodge
*My original concept for Dusk was to take assassin, but the way he’s been played leans more towards swashbuckler.

The first thing that immediately jumps out is that Dusk is a much deadlier fighter than Shady. Yes, if she can get the drop on Dusk and land a big sneak attack up front, that’ll surely hurt. But with that Alert feat, Dusk is almost guaranteed to be going first, and even if his individual attacks hurt less, he’s going to be doing more and occasionally hitting just as hard as Shady does with that increased crit range. Dusk is also more durable, thanks to his shield. To get in a third attack, Shady has to give up her cunning action, although with both of them being swashbucklers, there’s going to be a lot of hit-and-fade going on that makes cunning action superfluous. Also, Shady has to use Blade Flourish to bump her AC or damage output, and she only has 3 uses of that in any given fight.

On the other hand, Shady has a lot more flexibility and potentially fight-ending abilities, particularly Charm Person and Hold Person. Dusk’s high Wis save and Indomitable strengthen him against that, but Shady’s Lucky feat could then come along and say “Nope!” Heck, if Shady can get Dusk below 40 hp and drop a third level Sleep spell on him, that’s all she wrote.

In terms of the party, Shady is definitely a better leader and a lot more useful in social or exploration situations, while Dusk is more purely a striker. And the truth of the matter is neither one is likely to be interested in fighting the other one to the death. Dusk would probably be hitting on Shady the whole time, while Shady would be focused on whatever achieving goal Dusk stood in the way of and be looking for a way around him. But if they had to fight for some reason, I’d call their chances about even, maybe favoring Dusk just a bit but not much.

Which honestly? Seems about right. Shady is Jack Sparrow, while Dusk is Inigo Montoya.

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