Being a Pirate is Really Badass (Ugarit)

"Can't ask for a more interesting job with steady pay, I say!" said Lacia in reply. "You're a guitarist, are you? I've tried my hand at it personally, though it never really came easily, so I didn't get quite far... Well, I foresee many good times to be shared amongst the men - and, hell, maybe some of the women! - with a beautiful talented madame such as yourself on board." Lacia smiled and tilted his head to the side as he did so, a release of some of his cheerful energy in expressive movement.

Zach made his way to the ships helm,
"Listen up crew!" He yelled over the nattering seamen.
"We are headed for a poorly guarded merchant ship, apparently their escort was eaten by some kind of sea monster and only a few on board survived. It may easy money but I want everyone to get used to The Nave del Partido before we go robbing huge fleets.
I assume you all know your jobs so I suggest you get started on them."

It had only been a few minutes between Groh sitting down to sleep and the Captian yelling about what the plan was. It sounded good to him, but Groh had no idea what a first mate was supposed to do as the ship was about to embark. This didn't bother him too much, being as fucked up as he was at the moment, so he just stood up and leaned against the mast, waiting for a moment of inspiration to come to him, hoping he looked like he knew what he was doing.

After a uneventful five day journey (made more enjoyable for the presence of Annah and her music, among other charms, and by the fact that the cook apparently wasn't secretly substituting long pork for pork and seemed to understand that cooking involved more than 'apply fire to raw food') the Nave del Partido arrived at the intercept point.

Within an hour, Captain Zach was able to find the merchantship Vanessa had said should be passing by. It was apparently as the prostitute on Latoti had said; lightly armed, without escort, and baring some signs of damage that suggested less pirates and more sea monster.

The Nave del Partido was able to get within 300 feet of her before the ship seemed to notice, immediately attempting to sail away from the pirate boat.

Zach was trying to sweet talk Annah when he heard the ship was in sight. He immediately shot out to the main deck to bark his orders.
"Man the port Bastillae and shoot out their sails!" Zach drew his cutlass in preparation for boarding

SPOILER! :

Catapult Attack:1d20+6=14, 1d20+6=20
Ballista Attack: 1d20+4=10, 1d20+4=17, 1d20+4=15
Ballista Damage:2d8/2=6, 2d8/2=6, 2d8/2=6 18 total


Jobs notes:
CAPTAIN
Each round Zach must spend a standard action directing the ship and observing the battle.

HELMSMAN
Each round the helmsman - whoever that may be (probably Groh) must spend a standard action to steer the ship.

THE WATCH
Each round the sevven deckhands you hired must spend their standard actions doing various crap needed to make the ship do what it needs to do.

THE WEAPON TEAMS
Each round these guys each spend a full round action loading and firing weapons.

The merchant ship returned fire, three ballistae bolts impacting the Nave del Partido's rigging.
21 Damages to the rigging!

Having his new boat get scratched up so soon made Zach kind of annoyed. Regardless he carried on with his shouting.
"Shoot the cheeky bastards again!" He commanded the Ballista teams before stomping off to the front of the ship to swear at the merchants.

After a few rounds of fire later and Zach was grinning like an idiot as they drew closer to the crippled ship.

SPOILER! :

Ballista attack:1d20+2=6, 1d20+6=14, 1d20+6=25
Ballista damage:2d8/2=3, 2d8/2=3, 2d8/2=7 13 total

Okay. So the main point of this was to get some actual gameplay data on ship-to-ship combat. I've got that. I can already see what needs to be tweaked - namely the ease with which you can cripple another ship. The rigging sections are too easy to target for anyone with half a brain. I'll either up their HP or - more likely - up their AC. Either way, it's too easy. It may be realistic, but it's not particularly interesting or fun. I also intend to allow you to spend money to upgrade sails or something because as it stands now, two ships of the same class will literally never be able to catch eachother unless one is weighed down with cargo.
Basically the gist of the problem seems to come from the fact that WOTC's playtesters apparently didn't test shit at a higher level. At <5th level this would be more reasonable, but for 5< this is a bit too unpredictable.
Anyway, don't worry, you'll all get a chance to get bloody soon. I promise. Deal with it.

One of the ship's masts proceeded to fall over onto the boat, sending splinters everywhere and with screams and smashing noises audible even on Zach's ship.

About a second later the white flags came waving.

A cheer rang out on the ship. The enemy surrendered! What do?!

Groh had one hand holding the wheel steady and and the other keeping a firm grip on a bottle of rum. It was just too easy for him to steal booze from under the nose of that merlady. The Ballistas fired and the merchant ship took damage. Groh felt good about life.

The Captain had given no orders to him the change position, so Groh held the wheel steady, taking the occasionally swig of rum, with an almost child like grin plastered across his face.

Zach ordered for the ship to be driven up to a boardable distance and gave specific instructions.
"Board and steal mate's! Just don't kill anyone who is surrendering!"
Whether or not the crew listened to him regarding killing was anyones guess but they heard the boarding part okay.