This is an entry in the 'Dungeons & Data Science' series, a set of puzzles where players are given a dataset to analyze and an objective to pursue using information from that dataset.

Edited to add: Consensus is that this scenario is too complicated. It probably shouldn't be the first D&D.Sci scenario you play - try the original Voyages of the Gray Swan or The Sorcerer's Personal Shopper first, if you haven't played them yet.

Story

You had thought that the Admiralty was done with you after last time. After their response to your initial suggestions was to assign you to a series of dangerous voyages and hope that killed you, you were quite glad to set foot back ashore and not hear from them again. You've still been receiving a modest stipend for your past service for the last ten years or so, and that plus occasional odd-jobs for local wizards has left you a fairly comfortable life in the capital of Eastmarch.

So you are perhaps a bit concerned when you receive a summons to attend at once an audience with the Third Lord of the Admiralty. Your only consolation is that the summons arrives via a courier knocking on your door rather than a squadron of marines kicking it down and dragging you off.

You were not expecting what actually happened, though. When you were called into the Lord Admiral's office, there was only one person it it, and you recognized him.

"Captain O'Neill?" It's been a while since you saw him. He's still got the beard and the lively eyes, but he was wearing less braid back then, and a less...fancy...hat...

He chuckles. "It's Admiral now, actually. I'm sorry to call you here on such short notice, but a problem has arisen that I could use some help with."

It seems that Captain O'Neill (you absent-mindedly call him 'Captain' rather than 'Admiral' another three times during your conversation, but he doesn't seem offended) has risen through the ranks quite dramatically since you sailed with him on the Gray Swan. It also seems that he still remembers, and appreciates, your efforts to keep him and his crew alive ten years ago (even if your main motive was to keep yourself alive with them).

He explains that the Admiralty has an extremely important mission. Sometime later this week, ships need to reach certain locations on this MAP. He points out two locations.

You stare at the map in puzzlement. "Why do you want ships there? It doesn't look-"

O'Neill sighs. "Yes, I know. It is two random places in the middle of the ocean, that do not seem to be of any relevance. But Mage-Prince Konig is quite insistent that this is a vital objective, of such importance and secrecy that even I cannot be told what it is, and the First and Second Lords of the Admiralty concur with him. So I need to allocate two ships from those in port today to set sail tomorrow, one to each of those two locations, each carrying an unspecified cargo for unspecified purposes."

That...is odd. "So, if we stop at Norwatch here-"

The Admiral's teeth are gritted. "Yes. I know. The obvious way to address this is to transport whatever this unspecified cargo is to ports near the target locations using our standard supply routes, switch to a fresh vessel or await repairs, and then make short voyages from those nearby ports to the targets. However, a majority of the Admiralty Triumvirate-" (his tone of voice makes it very clear who that majority is) "-have decided that, for reasons of operational security, these voyages must launch from Eastmarch, must make their way to their respective destinations without stopping at other ports, and must return directly to Eastmarch afterwards."

You look at the map again. "That's...rather a long way."

O'Neill nods grimly and lowers his voice. "My fellow admirals have informed the Prince that the best ships in our Navy should be able to bring the cargo to those destinations without risk of mishap. I am less confident of this. And my fellow admirals believe that for the ships to successfully return afterwards is not entirely necessary. I disagree with this position, but I lack the authority to overrule them. But I remember what you've done before, and I'm hopeful that with access to the Admiralty archives you might be able to plot as safe a course as possible, and give my men the best chance they can have." He stands up straighter and looks you in the eye. "You've saved me and my men before. Will you do it again?"

Data & Objectives

In the Admiralty Archives, as well as the MAP you saw before, you find a LOG of the past voyages ships have made, and another LOG of the encounters recorded on them. You note approvingly that someone's been assigning ID numbers to the ships and voyages, so that you don't have to rely entirely on names.

June 1420, Week 1 has just ended. The next voyages will take place during June 1420, Week 2. The ships in port today (with you in the capital port of Eastmarch, Hex Q6) are:

The Bloody Diamond, a Barquentine captained by Angus MacDougal. Last voyage was 8 weeks ago.

The Orange Falcon, a Galleon captained by Brandon Buchanan. Last voyage was 7 weeks ago.

The Red Pearl, a Dhow captained by Brandon O'Malley. Last voyage was 6 weeks ago.

The Green Heart, a Dhow captained by Baron Heinrich von Reinhardt. Last voyage was 6 weeks ago.

The Purple Heart, a Dhow captained by Rick O'Neal. Last voyage was 5 weeks ago.

The Saucy Heart, a Barquentine captained by Erin Aubrey. Last voyage was 4 weeks ago.

The Rusty Heart, a Barquentine captained by Sir Gerhart von Zelig. Last voyage was 4 weeks ago.

The Mopey Diamond, a Carrack captained by Conall MacDougal. Last voyage was 3 weeks ago.

The Scurvy Hind, a Dhow captained by Dyllon Keating. Last voyage was 3 weeks ago.

The Mopey Tortoise, a Barquentine captained by Brandon O'Neal. Last voyage was 3 weeks ago.

The Red Duck, a Dhow captained by Conor Callahan. Last voyage was 3 weeks ago.

The Scurvy Swan, a Carrack captained by Seamus Reagan. Last voyage was 2 weeks ago.

The Silver Duck, a Carrack captained by Jack Keating. Last voyage was 2 weeks ago.

The Mopey Hind, a Barquentine captained by Angus MacDougal. Last voyage was 1 week ago.

The White Hind, a Dhow captained by Conor O'Connell. Last voyage was 1 week ago.

The Bloody Bottom, a Carrack captained by Lord Friedrich von Walderdorf. Last voyage was 1 week ago.

The Bloody Swan, a Carrack captained by Count Manfred von Konig. Last voyage was 1 week ago.

You need to choose one of those ships to journey to Hex E8 and one to journey to Hex L13, and assign routes to each of them. According to Admiral O'Neill, standard Admiralty practice would be to assign the Bloody Diamond and the Orange Falcon to these voyages, but you may assign any ships you see fit.

Most of the Admiralty believes that the most important objective is for both ships to successfully reach their destinations (regardless of whether they make it back afterwards), and that you should maximize that probability at all costs.

Admiral O'Neill would also like you to try to maximize how many of those ships are able to return safely home.

Which ship will you advise the Admiral send to each target? And what routes will you advise they take?

Bonus Objective: The Admiral's position seems politically tense. If you can find any useful information in the data, even if it's not strictly relevant to the mission at hand, it might help him improve his position.

Notes

This is based on abstractapplic's very good 'Dungeons and Data Science' series, and specifically on #4, 'Voyages of the Gray Swan'. You don't need to have played that one to do this, this one is using a very different ruleset. EDITED TO ADD: While it should be clear from the data, just to clarify for the particular avoidance of doubt: "Varsuuvius' Law of Random Encounters" as expounded in that scenario DOES NOT HOLD here.

Since the last few D&D.Sci scenarios have been pretty much completely solved, I've tried to give this one a more complex underlying world-model with a lot of different levels of success available. If you only have a little time to put into it, you should still be able to perform much better than random, but performing optimally is substantially harder - if you have a lot of time, as well as optimizing your success on the main mission there are a variety of secrets scattered in the data for the Bonus Objective.

For the sake of those who wish to work alone, please spoiler your comments if they contain information about the dataset, but you are also free (and encouraged) to work together.

I'll be posting the ruleset and answers in sometime between one and two weeks, depending on whether it looks like people are still working on this.