In the last part of the walkthrough, which you can read here, we left Homer swearing at the ocean for 12 hours, quite possibly in another dimension. When he’s finished, he miraculously reappears in front of the Entrance to begin the handover to the Sea Captain, who’ll be your guide for much of the remainder of the Squidport storyline.
1. The Old Man and the Sea Part 1: Homer steps out of his Squidport Entrance netherworld and notices something unusual in the distance:

Homer: No, it’s real! It’s some kind of house/boat hybrid! Hmmm, I wonder what you call that?
Um… a houseboat? And it comes with the Sea Captain for only $15000. It’s in your decorations menu rather than your build menu because there’s absolutely no wait time for it to build once you place it on your newly purchased water expansion. That means you unlock the Sea Captain (Horatio to his friends) right away.

2. The Old Man and the Sea Part 2: Make sure that you read the Sea Captain’s script in appropriately pirate-y language…
and possibly Homer’s as well. Get ready to welcome to Springfield a man who could seriously challenge Grampa in the rambling story-telling stakes:

Sea Captain: Y’arr, who be doing all that squalling and cussing at the sea? Ye made me sailors blush. Seriously, some of them cried.
Homer: Sorry, sometimes I have a potty mouth. Anyhoo, who the F@#& are you?
Sea Captain: Captain McCallister. Just let in from a long haul at sea. Been at Madagascar and Malabar and spent half a hundred days floating ’round the giant garrrbage patch in the Pacific. Y’arr, that last one tweren’t intentional. But sit ye down and have a yarn with the Captain. I’ll tell of a ship that near went under, her belly laden with counterfeit Kindle Fires.
Homer: Eh, I’m really not much for listening to people.
Sea Captain: Did I mention there’s be rum by the bucketfull?
Homer: Yarn away! Don’t leave anything out!
And so, the Sea Captain spends the next 4 hours telling tall tales. You don’t need to keep Homer free for this. Let him slip away and earn money for you – you’re going to need it.

3. Squidport Part 5: Finished with his tall tales, the Sea captain surveys what Homer has done with the Squidport so far…
Sea Captain: Ya’rr, the Squidport! This old seadog has spent many a silver here, having me caricature made and eating Dipping Dots. Tho something’s different now, can’t lay a finger to it. Wait, I have it – it’s become totally lame.
Homer: I know, right? You can’t buy a fried anything or squoosh a penny into a worthless flat oval.
Sea Captain: Me men’ll get this place into ship-shape. The finest builders what sailed the seas!
Lisa: It makes sense that sailors would know carpentry. They have to constantly repair the ship.
Sea Captain: Aye. We’ll start by building a logo store to increase footfalls and up the spill-over effect.
Lisa: Okay, now it’s making less sense.
Sea Captain: Sailors must also be well-versed in mall-science and neuromarketing.
And now it’s time to build you first Squidport shop – the Itchy and Scratchy Store. It becomes available at this point in your Building menu for $32000 and takes 24 hours to build. This can only go on the Boardwalk, and if you try to put it anywhere else, “the pirate guy will get mad”. Keep Bart and Milhouse free as the build finishes.

(T’s note: As you wait, resist the temptation to build too much Boardwalk – getting to far ahead on your Boardwalk progression seems to have a negative impact on the progression of the quest. There’s another glitch, too – the Store builds, but in some cases doesn’t clear from your task book. This is an easy glitch to fix, though, as putting the Store into your Inventory and taking it out again seems to get things moving.)
4. They Fight and Buy-It: Bart’s excited…

Milhouse: Yes! Luckily I went to the ER three times last month, so I’m flush with cash.
And off they go to spend four hours browsing the Itchy and Scratchy Store together. Unfortunately, it’s not all that they were hoping for:

Bart: This Itchy and Scratchy ball bounces funny and makes my eyes water when I smell it. Also, it’s stamped with the words “Warning: Not a Toy!”
Milhouse: I just found money in my other pocket.
Bart: What are we waiting for? Let’s buy more crap!
But that’s nothing for you to worry about – instead you can explore all the premium and non-premium items that unlocked with the completion of the Itchy and Scratchy Store. It’s over to the Sea Captain next to move the Squidport rebuild along.
The walkthrough will continue…
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