Shouldn't be hard; he's level 9 and it's CR 3.

Vencarlo gets a surprise round (though he loses initiative). Charging from hiding he almost can't miss.

Since he doesn't have Power Attack, and against a shadow divides his damage by two, Vencarlo won't do a lot of damage.

Pathfinder characters get more feats.[1] I say one of those feats should be Power Attack.

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1. In Pathfinder you choose a feat every other level, where in D&D 3.5 you get a feat every third level. So while the 6th-level Sable Company marines didn't gain feats from their conversion to Pathfinder, Vencarlo does. ↩

You need 13 Strength to qualify for the feat.

Besides, with the penalty to hit I'm not sure Power Attack would even do more damage -

Hrmm. Could you run the numbers both ways so I know what -

As entertaining as doing all that again would be, I'm afraid you don't qualify for the feat.

Round 75 (12:07:30)

For damage he rolls 1d6+1d6+6.[1] That's fifteen damage. Divided by two (and rounded down), it's seven.

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1. It's a +2 rapier, he has Weapon Training 1, but a penalty to Strength, Weapon Specialization adds +2, Precise Strike adds another +2, Sneak Attack adds 1d6. The d6s rolled 4 and 5. ↩

Out of the shadow's 19 hitpoints.

What's Vencarlo's touch AC?

While fighting defensively with Combat Expertise, 19.

Round 75 (12:07:30)

If you choose to take a -7 penalty to hit I'm going to start making you actually roll for that.

The shadow rolls 13 on the d20 and adds four, 17. Swing and a miss.

Round 75 (12:07:30)

No more sneak attack, but now Vencarlo can make two attacks in a round.

He has a +15/+10 bonus to hit with his rapier, or rather +8/+3. Neither attack hits.

Round 76 (12:07:36)

Shadow rolls a 12 on the die, +4 is 16, but Vencarlo dodges. 19 touch AC is pretty much as high as it gets, in Korvosa.

Round 76 (12:07:36)

On this keen rapier, an 18 and 17 both threaten critical hits! Though only the first confirms. Together they deal... 12 points of damage, reducing old man Mauro Silanus to 0 HP!

If you didn't want to go to the Abyss, you should have tried harder not to get eaten by shadows.

Hey, Blackjack, give me a Perception check.

Rolled a 20. So. 19.

What's your flat-footed AC against touch attacks?

10.

Round 76 (12:07:36)

Take a point of strength damage.

Round 77 (12:07:42)

Vencarlo wheels to face the shadow that rushed him and strikes at it twice. Both miss.

Round 78 (12:07:48)

Sometimes shadows roll 17s, too. Does a 21 hit your touch AC?

Yes.

Take six points of strength damage.

Round 78 (12:07:48)

Vencarlo has 2 strength left. His sword and leather armor make for a heavy load; his armor class drops by 3.

He attacks twice. Two critical threats, both confirm. With his strength penalty, they do 4 damage and 5.

Nine points of damage out of the shadow's 19 HP.