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is surprisingly bad at fighting.
Surely it's possible to have a 10th level vigilante that can do more than a dozen points of damage on a hit and have an AC that doesn't mean that he'd get mowed down if he actually tried to fight a group of average street criminals or hellknights?
In all seriousness, I had him, along with a sidekick character that I added in (5th level snakebite brawler), intervene in Lamm's assault on the Longacre (my campaign is strongly modified based on Inspectre's), and the two of them were barely able to take down four CR 1 opponents in a half dozen rounds, at which point they were both knocked out. Unless I was missing something significant, Blackjack, as written in the book, can't fight his way out of a wet paper bag.
Has anyone had a go at respeccing him so that he can reasonably be considered to be a master fencer that could plausibly face down a squad of Hellknights or a small gang of criminals and win?
I made a vow to myself to not change anything in the module, and let me be honest it is hard sometimes. The original maidens and doctors were such a cake walk for my group they lost all fear of them. As for Blackjack yeah he is definitely weak, but he is also old and ready to retire. Not to mention not the real hero of this story. If you want to use him and Cressida or whoever later in the game I would suggest levelling them up rather than a full respec min/max build.
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Certainly a necro (at least it's the same year?), but I noticed some of the same issues ZanThrax did with Vencarlo as written. I decided to rebuild him, and he's a bit more combat effective this way. For anyone interested, his rebuilt stats are below. This rebuild utilizes a 20-point buy.
XP 9,600
Male middle-aged human duelist 2 / swashbuckler (inspired blade) 1 / vigilante 7
CG / CG Medium humanoid (human)
Init +7; Senses Perception +12
DEFENSE
AC 22, touch 18, flat-footed 14 (+4 armor, +5 Dex, +3 dodge)
hp 69 (3d10+7d8+17)
Fort +4, Ref +13, Will +8
Defensive Abilities parry, unshakable (+7)
OFFENSE
Speed 30 ft., climb 15 ft.
Melee +2 defending rapier +17/+11 (1d6+9/15-20) or mwk dagger +15/+10 (1d4+7/19-20)
Ranged mwk dagger +15/+10 (1d4+7/19-20)
Special Attacks precise strike +2, startling appearance
TACTICS
Before Combat If confronted with peril in his social guise, Vencarlo does his best to retreat to a place of privacy and safety to assume his vigilante guise.
During Combat In his social guise, Vencarlo fights defensively and attempts to escape to a place of hiding so he can become Blackjack. In his vigilante guise, he is much more dangerous and aggressive. He begins fights with attempts to disarm his foes. If reduced to fewer than 30 hit points, he uses Combat Expertise and allocates bonuses from his +2 defending rapier to his AC, and focuses on simple attacks to defeat enemies.
Morale Vencarlo flees any battle where he's outnumbered more than three to one (unless he's attempting to right a great injustice). He also flees combat if reduced to fewer than 10 hit points, taking advantage of his climb speed to create quick distance.
STATISTICS
Str 11, Dex 20, Con 12, Int 14, Wis 10, Cha 15
Base Atk +10; CMB +10 (+12 disarm); CMD 26 (28 vs. disarm)
Feats Dodge, Combat Expertise, Fencing Grace (rapier), Improved Critical (rapier), Improved Disarm, Iron Will, Weapon Focus (rapier)
Skills Acrobatics +23, Bluff +15, Climb +12, Craft (blades) +6, Diplomacy +6 (+10 in social identity), Disguise +10, Escape Artist +18, Intimidate +10, Knowledge (local, nobility) +10, Perception +12, Perform (dance) +7, Sense Motive +13 (+17 in social identity), Sleight of Hand +12, Stealth +18, Swim +12
Languages Common, Elven, Varisian
SQ deeds (derring-do, dodging panache, opportune parry and riposte), inspired panache (4), dual identity, exceptional wealth, improved reaction, inspired finesse, seamless guise, social talents (great renown, renown, safe house [Vencarlo's home], social grace [Diplomacy, Sense Motive]), vigilante specialization (avenger), vigilante talents (cunning feint, rooftop infiltrator, sure-footed)
Gear +2 slick leather armor, +2 defending rapier, +1 rapier, mwk daggers (12), belt of incredible dexterity +2, amulet of proof against detection and location, bag of holding (type 1), boots of elvenkind, cloak of elvenkind, gloves of swimming and climbing, noble's outfit, gold signet ring (worth 250 gp), 34 pp, 29 gp
Canny Defense (Ex) When wearing light or no armor and not using a shield, Vencarlo adds 2 points of Intelligence bonus as a dodge bonus to his AC while wielding a melee weapon. If caught flat-footed or otherwise denied his Dexterity bonus, he also loses this bonus.
Deeds
Derring-do (Ex) Vencarlo can spend 1 panache point after rolling an Acrobatics, Climb, Escape Artist, Fly, Ride, or Swim check to add 1d6 to his result. On a 6, he can roll another d6 and addthat result too. This process continues as long as he continues to roll 6 up to a total of 4d6.
Dodging Panache (Ex) When an opponent attempts a melee attack against Vencarlo, he can spend an immediate action and 1 panache to move 5 feet, gaining a +2 dodge bonus against that attack (though not negating it). All other enemies who threaten Vencarlo can make attacks of opportunity.
Opportune Parry and Riposte (Ex) When an enemy attempts a melee attack against Vencarlo (but before it rolls its attack roll), he can spend an attack of opportunity and 1 panache to make an attack roll as if he was making an attack of opportunity with a -2 penalty for every size larger than Vencarlo the enemy is. If Vencarlo's result is higher than the enemy's, the attack misses, and he can spend an immediate action to make a counterattack against that enemy, as long as he can reach it.
Dual Identity (Ex) Vencarlo has a secondary identity as the fearless hero Blackjack. He can spend 1 minute to change identity. Any attempts to scry or otherwise locate Vencarlo only work if he is currently in the identity the creature is attempting to locate.
Parry (Ex) When Vencarlo takes a full attack action with a light or one-handed piercing weapon, he can elect not to take one of his attacks. At any time before his next turn, he can attempt to parry an attack against himself or an adjacent ally as an immediate action. To parry the attack, Vencarlo makes an attack roll, using the same bonuses as the attack he chose to forego during his previous action. If his attack roll is greater than the roll of the attacking creature, the attack automatically misses. For each size category that the attacking creature is larger than Vencarlo, he takes a -4 penalty on the attack roll. He also takes a -4 penalty when attempting to parry an attack made against an adjacent ally.
Precise Strike (Ex) When wielding a light or one-handed piercing weapon, Vencarlo adds his duelist level to the damage roll. He cannot attack with a weapon in his other hand or use a shield. This only works against living creatures with discernable anatomies. Any creature that is immune to critical hits is also immune to a precise strike.
Seamless Guise (Ex) Should anyone suspect Vencarlo of being anything other than what he appears to be in either his social or vigilante identity, he can attempt a Disguise check with a +20 circumstance bonus to appear as his current identity.
Social Talents
Great Renown (Ex) Vencarlo gains a +6 circumstance bonus on Intimidate checks whenever he is in his vigilante identity of Blackjack while in the city of Korvosa.
Startling Appearance (Ex) Whenever Vencarlo attacks a foe that is completely unaware of his presence, the foe is treated as flat-footed for the rest of the vigilante's turn (uncanny dodge or a similar ability prevents this effect unless Vencarlo's vigilante level is at least 4 levels higher than the foe with uncanny dodge). The foe also takes a -4 penalty on attacks made against Vencarlo until the start of Vencarlo's next turn.
Unshakable (Ex) Vencarlo adds his vigilante class level to the DC of any attempts to Intimidate him.
Vigilante Talents
Cunning Feint (Ex) Vencarlo can feint as a move action or in place of his first attack during a full attack.
Sure-Footed (Ex) Vencarlo can move at full speed while using the Stealth and Acrobatics skills without penalty.
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I did rebuild him as well. Stayed straight vigilante 10.
Take 'Em Alive lets him use non-lethal damage at all times, which means that he triggers Enforcer on every attack, which triggers Twisting Fear, and opens up Shatter Defenses so that he can land hidden strike damage, which triggers Violent Display so that he can use immediate actions to hit everyone in the area with Twisting Fear damage.
Think Batman dropping into a dark room full of thugs, and hitting the first one so hard that all the rest are so terrified that it hurts.
"WHAT ARE YOU?"
"I'm Vengeance"
Blackjack CR 9
XP 6,400
Human (Chelaxian) vigilante 10 (Pathfinder RPG Ultimate Intrigue 9)
CG Medium humanoid (human)
Init +4; Senses Perception +12
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Defense
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AC 17, touch 16, flat-footed 13 (+2 deflection, +4 Dex, +1 natural)
hp 78 (10d8+30)
Fort +8, Ref +14, Will +9
Defensive Abilities unshakable (+10)
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Offense
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Speed 30 ft.
Special Attacks hidden strike +5d8/+5d4, startling appearance
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Statistics
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Str 14, Dex 18, Con 14, Int 10, Wis 8, Cha 12
Base Atk +7; CMB +9; CMD 25
Feats Dazzling Display, Enforcer[APG], Shatter Defenses, Skill Focus (Acrobatics), Skill Focus (Intimidate), Violent Display, Weapon Finesse, Weapon Focus (rapier)
Skills Acrobatics +23, Bluff +5, Climb +10, Diplomacy +9, Disguise +5 (+25 to appear as part of polite society while in your social identity), Escape Artist +9, Intimidate +20 (+26 in your Korvosa while in your vigilante identity), Knowledge (local) +9, Knowledge (nobility) +9, Perception +12, Sense Motive +3, Sleight of Hand +9, Stealth +17, Swim +6
Languages Common
SQ dual identity, social talents (discrete inquiries, great renown[UI], quick change[UI], renown[UI], safe house[UI]), vigilante specialization (stalker[UI]), vigilante talents (lethal grace[UI], perfect fall[UI], take 'em alive, twisting fear[UI], up close and personal[UI])
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Special Abilities
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Dazzling Display (Rapier) Intimidate check to demoralize can affect those within 30' who see you.
Discrete Inquiries (Ex) You can gather information without being obvious that you are seeking it.
Dual Identity (Ex) Each identity maintains own alignment, can switch over 1 min. Magical means treat an ID as non existant while not adopted.
Enforcer If you deal nonlethal damage with a melee weapon, make a free Intimidate check to demoralize.
Hidden Strike +5d8/+5d4 Extra damage vs. unaware/startled foes, less vs. flat-footed/flanked foes.
Perfect Fall (Ex) No dam from fall if in reach of a wall, half dam otherwise. Always land standing.
Quick Change (Ex) Change ID as a full-round action, but easier to detect unless take 1 rd more.
Renown +6 (Korvosa) (Ex) Renowned in one community of up to 5,000 people, or two of up to 2,000 each.
Safe House (1,000,000 cu. ft.) (Ex) Gain safe area protected from divinations. If have renown, can move it around area of renown.
Startling Appearance (Ex) Attacking unaware foe makes them flat-footed and they -4 to attack you for 1 rd.
Take 'Em Alive +3 (Ex) No pen on nonlethal att. Bonus to att & dam if only deal nonlethal dam (no 2nd effects).
Twisting Fear 5d4 (Ex) Causing foe to be shaken, frightened, or panicked inflicts listed nonlethal dam.
Unshakable +10 (Ex) Add the listed bonus to the DC of foes attempting Intimidate checks against you.
Up Close and Personal +5d8/+5d4 (Ex) As a swift action when use Acrobatics to move through foe space, make att with hidden strike dam.
Violent Display Use Dazzling Display as immediate action after critical hit or sneak attack.
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Honestly, I think it sorta made sense that he was a bit of a pushover, even though he's level 10, he mainly fight low tier thugs, and he's still a middle-aged, pushing old man that runs a school now instead of actively fighting crime like he did in his prime.
But those could definitely be him in his prime.
I did rebuild him as well. Stayed straight vigilante 10.
Take 'Em Alive lets him use non-lethal damage at all times, which means that he triggers Enforcer on every attack, which triggers Twisting Fear, and opens up Shatter Defenses so that he can land hidden strike damage, which triggers Violent Display so that he can use immediate actions to hit everyone in the area with Twisting Fear damage.
Think Batman dropping into a dark room full of thugs, and hitting the first one so hard that all the rest are so terrified that it hurts.
"WHAT ARE YOU?"
"I'm Vengeance"Blackjack CR 9
XP 6,400
Human (Chelaxian) vigilante 10 (Pathfinder RPG Ultimate Intrigue 9)
...
I've been trying to recreate your version in Hero Lab - and it's not working.
More than the standard 15 points have been used and/or you've given Vencarlo some stat-increasing gear, the skill points don't quite fit (although that might be due to Vencarlo not being equipped with his Gloves of Swimming and Climbing), and this version has one feat too many. Furthermore, the ACs, saving throws, and some other derived stats don't match the Vencarlo version in your post. I also had trouble finding the Violent Display feat until I tracked it down to Blood of the Moon (where it's associated with were-tigers and their kin and associates). (That's an interesting background choice for Vencarlo! Could it be one of the reasons for his dislike of the Arkonas?)
Did you change his gear or anything else of note?
I must admit that I found it hard to visualise this version of Vencarlo as a renowned Kovosan fencing master when his Bluff and Sense Motive skill modifiers were so abysmal. (Making and resisting Feints in combat - part and parcel of fencing - require those two skills.)
Incidentally, I also discovered that whoever input the Inner Sea Intrigue vigilante talents into Hero Lab originally, that person apparently didn't know the difference between "discreet" and "discrete". :)
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There is a discrete difference between the behavior and characters of those who are and are not discreet.