"What the hell is going on Skeetz? Where'd you drag this guy up from?"
Ha! I wrote that last sentence then opened Kit's character sheet to see what his Insight modifier is.
Rolls
Insight - (1d20-1)
(11) - 1 = 10
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Insight - (1d20-1)
(11) - 1 = 10
Ready action to fire if the man doesn't stay "surrendered" w/ DA in case he's out of short range - (1d20+9, 1d20+9, 1d6+5)
1d20+9 : (8) + 9 = 17
1d20+9 : (16) + 9 = 25
1d6+5 : (2) + 5 = 7
Hunter's Mark extra damage - (1d6)
(1) = 1
Readied strike with maul if guard doesnt choose the justice option. - (1d20+5)
(12) + 5 = 17
Damage if necessary - (2d6+3)
(21) + 3 = 6
Con save (DC 5) - (1d20+2)
(13) + 2 = 15
Persuasion (with advantage for those charmed) - (1d20+3, 1d20+3)
1d20+3 : (8) + 3 = 11
1d20+3 : (3) + 3 = 6
Wisdom saving throw DC 13 - (1d20+0)
(8) = 8
Stealth - (1d20+5)
(10) + 5 = 15